Tax hit
Determining and supporting deductions is complex for those not well-versed in federal and state rules and regulations, not to mention differentiating between the two. As it does ever year, the Minnesota Society of CPAs recently surveyed its CPA members about the most outrageous tax deductions clients tried to claim on their tax returns.

"Creativity is a beautiful trait to embrace, but there are better places to exercise yours than with your CPA and the IRS," said MNCPA Board Chair Jeff White. "Tax laws are very nuanced, but many of the deductions our members shared from their clients would create issues with the IRS."

The following list shows that, quite often, taxpayers don't know which deductions are allowed or not. Here is the MNCPA's annual list of the most outrageous, and unacceptable, deductions.
Tummy tuck
1. Tummy tuck
One CPA had a client who wanted to deduct an abdominoplasty—more commonly known as a "tummy tuck"—as a medical expense because of the amount of money she had to spend on the procedure. No dice.
Dream home
2. Building your dream home
As a contractor, one client talked to their CPA about writing off the cost of building themselves a new house. That one didn't get off the ground.
Solo lunch
3. All by myself (for lunch)
One client tried to claim mileage for 25 roundtrips to a restaurant for lunch with himself. Put a fork in this idea.
Family vacation
4. Working vacation?
One client tried to deduct expenses for a family vacation to Disney because he "was working the whole time." Let's hope Disney hired him—he's got a great imagination.
Pontoon boat
5. Boats (again)
A nearly annual addition to this list, one client wanted to deduct his pontoon as an advertising expense because he occasionally took out clients for a cruise. Sunk.
Mexican dentists
6. Dental work across the border
This one is a doozy. One CPA had a client who flew to Mexico—multiple times—for dental work and, in their infinite wisdom, thought they could extract the difference via deductions. There was no bridging this idea.
Swimming pool maintenance
7. Pools don't make good offices
Repairs and maintenance to an in-ground pool, as one client found out, cannot be used as a home office deduction. The CPA had to drown out this idea.
giving cash from wallet
8. Stretching charity
While helping out family members with monetary gifts is kind, it is, however, not legally classified as charitable donations. Do you think they at least got a receipt?
Fur coat window
9. High-class cleaning
This is a new one. One CPA had a client who wanted to deduct the cost of her fur coat because she wore it to keep warm as she cleaned homes. Talk about a faux idea.
football fans watching game on TV
10. Super Bowl gambling loss: $2
That's not a misprint. One client wanted to file for a gambling loss on a $2 bet on the Super Bowl. While gambling losses can be deducted by following instructions from the IRS, $2 leaves a bit to be desired. Better luck next year.