Archive for the ‘Massachusetts’ Category

The Almost-End of the 2023 Tax Season

Thursday, November 16th, 2023

It’s been a while since I posted: family issues, tax deadlines, and paper in every direction has made me concentrate on serving my clients, and not the blog.  I’ll have a recap of the 2023 Tax Season soon, but today is a celebratory day: Today is the almost-end of the 2023 Tax Season.  Thursday, November 16th is the filing deadline for California taxpayers (except for four counties in the northeast portion of the state).  I believe we have one signature document outstanding, but otherwise our outstanding California returns were filed.

It’s not the end of the 2023 Tax Season, though: taxpayers impacted by hurricanes in Florida (most of the state except for the Miami-Palm Beach area), South Carolina, Maine, and Massachusetts have until Thursday, February 15, 2024 to file their extended 2022 tax returns.  We have four such clients.

The IRS will be turning off electronic filing of individual returns this weekend until sometime in January.  The ancient IRS computer system (it dates to 1959) takes two months or so to be reprogrammed for the following year taxes.  If you need to electronically file a 2020 tax return (or a 2020 amended return), now is a great time to do so because after Friday you won’t be able to.

I’ll also soon have a preview of the upcoming paperwork tsunami disaster and what it means for both the 2024 Tax Season and Automated Underreporting Unit notices in 2025.

Maine & Massachusetts Conform to IRS Hurricane Extension

Wednesday, October 4th, 2023

In the US we have a dual system of taxation: federal and state taxes.  Of course, you can be a resident of a state without state income tax like me and not have to deal with state income taxes, but most Americans file two returns. On September 26th the IRS announced they were extending tax filing deadlines for all taxpayers residing in Maine and Massachusetts because of Hurricane Lee. But states do not have to follow federal extensions (New York, for example, recently did not conform to a federal disaster declaration).

I called both the Massachusetts Department of Revenue and the Maine Department of Revenue Services.  Both states are conforming to the federal extension.  There is one additional step needed for taxpayers in Massachusetts: You need to write “STORM” at the top of your Massachusetts return.

This is good news for those impacted by the hurricane.  Do note this is just an extension of time to file, not pay.

Bozo Tax Tip #5: Procrastinate!

Monday, April 11th, 2022

Today is April 11th. The tax deadline is just seven days away.

What happens if you wake up and it’s April 18, 2022, and you can’t file your tax? File an extension. Download Form 4868, make an estimate of what you owe, pay that, and mail the voucher and check to the address noted for your state. Use certified mail, return receipt, of course. And don’t forget your state income tax. Some states have automatic extensions (California does), some don’t (Pennsylvania is one of those), while others have deadlines that don’t match the federal tax deadline (Hawaii state taxes are due on April 20th, for example). Automatic extensions are of time to file, not pay, so download and mail off a payment to your state, too. If you mail your extension, make sure you mail it certified mail, return receipt requested. (You can do that from most Automated Postal Centers, too.)

By the way, I strongly suggest you electronically file the extension. The IRS will happily take your extension electronically; many (but not all) states will, too.  If you make an extension payment on IRS Direct Pay (using “Extension” as  the reason for the payment), the IRS will file an extension for you.

But what do you do if you wait until April 19th? Well, get your paperwork together so you can file as quickly as possible and avoid even more penalties. Penalties escalate, so unless you want 25% penalties, get everything ready and see your tax professional next week. He’ll have time for you, and you can leisurely complete your return and only pay one week of interest, one month of the Failure to Pay penalty (0.5% of the tax due), and one month of the Failure to File Penalty (5% of the tax due).

There is a silver lining in all of this. If you are owed a refund and haven’t filed, you will likely receive interest from the IRS. Yes, interest works both ways: The IRS must pay interest on late-filed returns owed refunds. Just one note about that: the interest is taxable.

(Note: If you reside in Massachusetts or Maine, your tax filing deadline for 2021 returns is Tuesday, April 19th.  Thanks to Patriot’s Day you get an extra day this year to file your tax returns and/or extensions.)

Out With the Fed Mandate; In With State Mandates

Wednesday, November 13th, 2019

Once upon a time there was the federal mandate to have health insurance; per the US Supreme Court, a “tax.” Well, beginning with 2019 tax returns (filed in 2020) the federal mandate is no more. Unfortunately, tax professionals and taxpayers aren’t done with insurance mandates: Several states have implemented their own mandates.

Massachusetts, New Jersey, and the District of Columbia have their own mandates for the 2019 tax year (tax returns filed in 2020); Massachusetts’ mandate began in 2007. California, Rhode Island, and Vermont have implemented mandates for the 2020 tax year (tax returns filed in 2021).

If you are a resident of one of these states, we’ll be asking you about health insurance when we prepare your 2019 returns. Additionally, if you do receive insurance through the Exchange (e.g. healthcare.gov) and receive a Form 1095-A, you must provide a copy of the form to your tax professional.

There’s no reason for tax professionals to be in the health insurance field. But thanks to Obamacare, we are…and will be for the foreseeable future.

Can a California or Massachusetts Professional Gambler Take a Business Loss on His or Her State Tax Return?

Tuesday, March 19th, 2019

The Tax Cuts and Jobs Act (TCJA) eliminated the ability of a professional gambler to take a loss on his Schedule C based on his business expenses; Congress specifically overrode the Mayo v Commissioner decision. But what about state taxes? Can a professional gambler who had a losing year take a loss on those returns?

First, no professional gambler can take a loss based on his gambling results. Internal Revenue Code Section 165(d) prohibits gambling losses in excess of wins. Every state with a state income tax conforms to this.

But state conformity to the TCJA is decidedly mixed. California does not conform to almost any part of the TCJA. The Franchise Tax Board produced a publication showing each change in law and the impact to California. At the bottom of page 89 is the beginning of the discussion on Section 11050 of the TCJA (which changed the rules for professional gamblers). The FTB publication notes:

California conforms, under the PITL, to the federal rules relating to the deduction for losses from wagering transaction[s] under IRC section 165(d), as of the specified date of January 1, 2015, but does not conform to the federal limitation on the deduction.

Thus, a California professional gambler can take a loss based on his business expenses on his state tax return.

Massachusetts also doesn’t conform to federal law in this area. However, Massachusetts does not allow losses from any business to be reported on its tax returns. Thus, a Massachusetts professional gambler wasn’t able to take a loss based on his business expenses in the past and cannot today.

State conformity on the provisions of the TCJA will vary among the states. If you reside in or must pay state taxes, this is a key issue that you must discuss with your tax professional.

Boston Bruins 2, IRS 0

Monday, June 26th, 2017

Bruins Logo

The United States Tax Court today looked at whether pregame road meals for a National Hockey League (NHL) team are “meals and entertainment” expense (which would be deductible at 50% of cost) or a “de minimis fringe” and deductible at 100% of cost. As you might be able to guess from the title of the post, the Bruins shutout the IRS today.

First, if you’re interested in some of all of the background work that must be done for hockey, the opinion is a must-read. For example, I did not know that the road team in hockey does not receive any of the ticket revenue for regular season games. But I digress….

The IRS allowed pregame home meals but did not allow pregame road meals as a de minimis fringe; the IRS claimed that road (away) meals were a meal and entertainment expense. Of course, the meals must also be business-related but both the IRS and the Bruins agreed on that. As you might imagine, diet matters to NHL players:

Each away city hotel prepares pregame meals (i.e., breakfast, lunch, or brunch) and snacks that meet the players’ specific nutritional guidelines to ensure optimal performance for the upcoming game and throughout the remainder of the season. The Bruins contract in advance with each away city hotel for the provision of pregame meals and snacks, and the food is made available to all traveling hockey employees. The Bruins initiate the meal contracting process by providing a custom meal menu to the prospective away city hotel requesting specific types and quantities of food. The Bruins tend to keep food options consistent at each away city hotel to avoid players’ having gastric problems during the game. The Bruins always order the same quantity of food to feed all traveling hockey employees.

The de minimis fringe exception first requires that the eating facility be available to all, and not discriminate in favor of highly compensated employees. NHL teams bring a lot more than just the players on a road trip:

During the years in issue the Bruins traveled to away games with various personnel, which typically included: between 20 and 24 players, the head coach, assistant coaches, medical personnel, athletic trainers, equipment managers, communications personnel, travel logistics managers, public relations/media personnel, and other employees (traveling hockey employees). During the years in issue the Bruins’ traveling hockey employees traveled to every away game.

The Bruins easily passed this first hurdle because the food was provided to all. The major issue was whether these were a de minimis fringe benefit:

Employee meals provided in a nondiscriminatory manner constitute a de minimis fringe under section 132(e) if: (1) the eating facility is owned or leased by the employer; (2) the facility is operated by the employer; (3) the facility is located on or near the business premises of the employer; (4) the meals furnished at the facility are provided during, or immediately before or after, the employee’s workday; and (5) the annual revenue derived from the facility normally equals or exceeds the direct operating costs of the facility (the revenue/operating cost test).

The Bruins lease hotel facilities; that would make it appear that they would pass the first test. “The evidence establishes that the Bruins contract with away city hotels for the right to “use and occupy” meal rooms to conduct team business, and therefore these agreements are substantively leases.” And given that they contract with the hotel to provide the food, they meet the operating test.

It appears (from the opinion) that the IRS vigorously opposed the idea that the Bruins passed the “facility is located near the business premises of the employer” test. But the Court disagreed.

First and foremost, the nature of the Bruins’ business requires the team to travel to various arenas across the United States and Canada, and it is not feasible for the Bruins to be a viable NHL franchise without participating in hockey games outside of Boston. The NHL constitution and bylaws obligate each NHL team to play both home and away games during the regular season and, if the team qualifies, postseason games. Not only does the NHL require teams to participate in away games, but it also requires visiting teams to arrive in an away city at least six hours before the away game commences. The CBA imposes an additional requirement that visiting NHL teams travel to the away city the day before game day, if travel by airplane is greater than 150 minutes. Furthermore, if an NHL team fails to participate in an away game it must forfeit the game, lose playoff points, incur financial penalties imposed by the NHL, and indemnify the home team for loss of revenue and other expenses. Therefore, an integral part of the Bruins’ professional hockey business involves traveling throughout the United States and Canada to play away games as dictated by the NHL schedule. The job of the Bruins’ team includes playing one-half of their regular season games away from their hometown arena, and the financial health of the NHL franchise–not to mention the NHL itself–would be adversely affected if teams refused to play away games.

The Court ruled that staying in away city hotels was essential for the Bruins, and it’s clear that it would be impossible for the Bruins to do all this in Boston. “The evidence at trial also establishes that the Bruins could not perform all these activities at the opponent’s arena because of limited access and insufficient space and facilities.” Thus, the Court held that the road hotels were part of the Bruins’ business premises.

The IRS disagreed:

[T]he traveling hockey employees’ activities at away city hotels are insignificant because: (1) the activities at away city hotels are qualitatively less important than playing in the actual hockey game and (2) the Bruins spend quantitatively less time at each away city hotel than they do at the team’s Boston facilities.

The Court, though, thought that the IRS was offsides on these arguments.

Without the preparatory activities that occur at away city hotels the Bruins’ performance during games would likely be adversely affected. Furthermore, respondent provides no precedent to support the argument that business premises are limited to the location where the most qualitatively significant business activity occurs…Although the Bruins do spend quantitatively less time at each individual away city hotel than they do in Boston, this goes to the unique nature of a professional hockey team that is required to play one-half of its games away from home. It is therefore illogical for respondent to ignore the nature of the Bruins’ business and the NHL and analyze the amount of time spent at each away city hotel in isolation.

The Bruins also passed the revenue/operating cost test. “Meals are excludable to recipient employees under section 119 if they are (1) furnished for the convenience of the employer and (2) furnished on the business premises of the employer.” And the Court agreed with the Bruins here:

The evidence establishes that the pregame meals at away city hotels are provided to the Bruins’ traveling hockey employees for substantial noncompensatory business reasons. The Bruins provide pregame meals to traveling hockey employees at away city hotels first and foremost for nutritional and performance reasons…Providing meals to traveling hockey employees at away city hotels enables the Bruins to effectively manage a hectic schedule by minimizing unproductive time (e.g., finding and obtaining appropriate meals from restaurants in each city) and maximizing time dedicated to activities that help achieve the organization’s goal of winning hockey games. Petitioners have provided credible evidence establishing the business reasons for furnishing pregame meals to traveling hockey employees at away city hotels, and we will not second-guess their business judgment.

The IRS conceded the last part of the test (that the meals were furnished during, before, or after the workday). Thus, it was a shutout: Bruins 2, IRS 0 (the petitioners, the owners of the Bruins, were challenging an IRS audit covering two tax years).

Other professional sports teams may be filing amended returns (if they had only been taking half of the cost of meals) because it’s hard to imagine that the requirements for, say, a traveling NFL or NBA team aren’t similar to those of an NHL team. This is a full decision of the Tax Court, so it is precedential.

Case: Jacobs v. Commissioner, 148 T.C. No. 24

Update on the Future of Daily Fantasy Sports

Thursday, November 19th, 2015

So far, I’ve been accurate on my predictions. Back in February 2014 I wrote,

Unfortunately, many states look at just an element of chance to determine if something is gambling. And there’s no doubt that daily fantasy sports have such an element. The problem is that these sites are starting to bring in large dollars. That attracts attention, and some state attorney general is going to wonder the same thing that I am. He or she will conclude that the Duck Test applies and that these are gambling sites in violation of his or her state’s laws. [emphasis in original]

Last month I wrote,

I expect DFS to follow two different paths in the majority of states. Some states will simply declare it as gambling, making it effectively illegal in those states. Other states will tacitly declare it as gambling but allow regulation of the activity. There will be a minority of states that allow DFS to continue as an unregulated activity. Where one month ago you could play DFS in 45 of the 50 states, that number is down to 42 to 44 states (depending on the DFS site). I expect that number to continue to fall.

Events have moved faster than I thought they would. The New York Attorney General declared DFS to be gambling, and has asked a court for an injunction. One of the two major sites, FanDuel, has stopped offering contests for New Yorkers. The hearing will be next Wednesday. The Massachusetts Attorney General has proposed regulations.

As for New York, I think FanDuel is operating far wiser than DraftKings. DraftKings is still allowing New York residents to play on the site. Given that there is a non-zero chance that the company will find it outself ordered to stop, and that operating in violation of state law would be a predicate offense for possible federal charges, I think DraftKings is making the wrong decision. (I will point out again that I am not an attorney, and nothing I’m writing should be construed as legal advice.) If you ask me the most likely result of the New York Attorney General’s action, it’s that the sites will find themselves enjoined from serving New York customers. This isn’t a certainty, but if you’re going to place a bet on the results that’s the favored side.

I still think we will end up with a dichotomy within the states. States that are notoriously anti-gambling or have constitutional provisions against gambling (including much of the South: Texas, Florida, and Tennessee; Utah, and Hawaii) will ban DFS, either by Attorney General rulings or by court actions. Other states will regulate DFS. Some states will order the DFS companies to shut down until regulations are in place. A very small number of states will just ignore the issue, and leave DFS in an unregulated state.

DFS proponents need to remember that a regulator’s first instinct when confronted with something new is to ban it. Add that to the fact that DFS is legal by way of a loophole (in the view of regulators) and you get a strong inclination for them to end DFS.

That’s the most likely outcome. However, there is still the chance that DFS could end completely. There are federal investigations of the sites which could, if indictments result, end the industry.

This is a fascinating story–and the greed of the sites has sped up the story line. It was inevitable that DFS would attract scrutiny. The pace of that scrutiny sped up because the sites went overboard in their advertising and had very poor visuals. We’ll all be able to see the future of this product unfold in the next few weeks.

State Financial Health: Alaska, Dakotas on Top, Illinois, New Jersey, Massachusetts and Connecticut on the Bottom

Tuesday, July 7th, 2015

The Mercatus Center at George Mason University released a study today ranking the 50 states on their financial health. Here are the top six states:

1. Alaska (8.26)
2. North Dakota (2.97)
3. South Dakota (2.84)
4. Nebraska (2.75)
5. Florida (2.74)
6. Wyoming (2.67)

These six states have “Fiscal Condition Index” scores that are significantly higher than all the other states. Of course, where there’s good there’s also bad; here are the bottom seven states:

50. Illinois (-1.86)
49. New Jersey (-1.86)
48. Massachusetts (-1.84)
47. Connecticut (-1.83)
46. New York (-1.49)
45. Kentucky (-1.42)
44. California (-1.41)

Why are states ranked low?

High deficits and debt obligations in the forms of unfunded pensions and health care benefits continue to drive each state into fiscal peril. Each holds tens, if not hundreds, of billions of dollars in unfunded liabilities—constituting a significant risk to taxpayers in both the short and the long term.

Think unfunded pensions and you have one of the huge issues facing states. Illinois leads the way (which isn’t a good thing for the Land of Lincoln). There’s a reality: Whatever you make, spend less. Some states follow that creed; others give it lip service. California may have a “surplus,” but when you look at unfunded pensions things don’t look so good. Sooner or later, that bill will come due.

It’s an interesting analysis, and well worth your perusal.

Massachusetts Has a New Software Sales Tax

Saturday, August 17th, 2013

Taxachusetts, er, Massachusetts has had for years a reputation of being a high tax state. Lately, Massachusetts has become a somewhat better locale (based on taxes). It’s not that Massachusetts has improved; rather, other nearby states have enacted or increased taxes. Just when you thought you could throw away the Taxachusetts label, out comes a new sales tax.

Last month, the Massachusetts legislature passed a new sales tax on computer software services. At 6.25%, it’s the highest sales tax rate on this in the country. The tax applies to all “computer software, including pre-written upgrades, which is not designed and developed by the author.” The law was effective July 31, 2013.

One website has published a piece about how confusing this new tax is. Consider:

This added levy is not only cumbersome, it’s super confusing. For example:

  • if you install software (Microsoft Office, Constant Contact, Drupal, etc.), it’s taxable
  • if your client clicks the mouse to install it, it’s not taxable
  • training your client to use this software is not taxable
  • but if you “customize” or configure the software in any way, it’s taxable
  • if you don’t actually make any changes, but just discuss them and plan them, it’s consulting and not taxable
  • if you create graphic design mockups, it’s not taxable
  • but as soon as you implement that design (i.e. program it), it becomes taxable if you’re using “prewritten” software “not developed” by you (such as WordPress)

At least, that’s how we think it works.

The Massachusetts high-tech community is up in arms over the new tax. As Christopher Anderson, president of the Massachusetts High Technology Council, said in an interview on WBZ-TV (as reported in the Boston Globe,

“When we impose a tax that no other state in the country imposes as broadly as this, it is going to have an impact on those small and midsize companies, initially, in terms of their ability to win and retain business or add or retain employees,” he said.

“In fact, a number of them are telling me they may have to shed employees just to maintain the business load they have,” Anderson added in the interview with WBZ’s Jon Keller.

Democratic state Senator Karen Spilka has filed a bill to repeal the measure. Meanwhile, Florida Governor Rick Scott has urged unhappy Massachusetts companies to consider moving to the Sunshine State. I am certain that if this tax remains law Massachusetts will see some companies move out-of-state. Taxes matter, and when a business in Massachusetts faces a confusing 6.25% tax while a business in neighboring New Hampshire doesn’t, a business owner might just move.

IRS Gives Extra Three Months for Filing and Payments to Boston-Area Taxpayers; Massachussetts Deadline Should be the Same

Wednesday, April 17th, 2013

As I’m still not really working, here’s the press release from the IRS:

WASHINGTON — The Internal Revenue Service today announced a three-month tax filing and payment extension to Boston area taxpayers and others affected by Monday’s explosions.

This relief applies to all individual taxpayers who live in Suffolk County, Mass., including the city of Boston. It also includes victims, their families, first responders, others impacted by this tragedy who live outside Suffolk County and taxpayers whose tax preparers were adversely affected.

“Our hearts go out to the people affected by this tragic event,” said IRS Acting Commissioner Steven T. Miller. “We want victims and others affected by this terrible tragedy to have the time they need to finish their individual tax returns.”

Under the relief announced today, the IRS will issue a notice giving eligible taxpayers until July 15, 2013, to file their 2012 returns and pay any taxes normally due April 15. No filing and payment penalties will be due as long as returns are filed and payments are made by July 15, 2013. By law, interest, currently at the annual rate of 3 percent compounded daily, will still apply to any payments made after the April deadline.

The IRS will automatically provide this extension to anyone living in Suffolk County. If you live in Suffolk County, no further action is necessary by taxpayers to obtain this relief. However, eligible taxpayers living outside Suffolk County can claim this relief by calling 1-866-562-5227 starting Tuesday, April 23, and identifying themselves to the IRS before filing a return or making a payment. Eligible taxpayers who receive penalty notices from the IRS can also call this number to have these penalties abated.

Eligible taxpayers who need more time to file their returns may receive an additional extension to Oct. 15, 2013, by filing Form 4868 by July 15, 2013.
Taxpayers with questions unrelated to the Boston tragedy should visit IRS.gov, or contact the regular IRS toll-free number at 1-800-829-1040.

Meanwhile, the Massachusetts Department of Revenue has extended the deadline until at least April 23rd. The press release states, “The IRS is expected to provide details on the federal extension shortly. DOR will match whatever extension the IRS announces.”

Thus, for taxpayers living in and around Boston (and individuals impacted by the bombings, including participants and first responders), they should not owe penalties. Interest, however, is statutory and cannot be waived. The Boston-area tax deadline will be Monday, July 15th.