I received a 1099-MISC for the winnings (recorded in box 3) and have read some of the related post here. I think my questions are a bit different.
(1) If I entered the 1099-MISC as "This was prize winnings" in the "Does one of these uncommon situations apply" screen, how/where to I enter the deductions? There seems to be very limited types of expenses this year and I don't even see a free-text "other deductions".
(2) As an option, if I entered the 1099-MISC and chose "None of these apply" in the "Does one of these uncommon situations apply?" screen, will not choosing "This was prize winnings" be a red flag for IRS. I saw other articles recommending to actually do this (i.e., choose "None of these apply") but I'm not so sure because it's technically "prize winnings".
(3) Follow up to #2, in doing it Turbo Tax makes bowling into a business. Will this be a problem?
(4) If I enter the winnings in "Prizes, Awards, and Gambling Winnings", this will allow me to enter deduction as "Gambling Losses". Question - will there be a problem because this means that I will not be entering the 1099-MISC? I will instead just enter the 1099-MISC box 3 amount in "other gambling or lottery winnings not reported on a W-2G". I read somewhere that IRS matches 1099-MISC copies they get with our tax returns so this may not be a good idea.
Any other options to deduct bowling expenses and entry fees?
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Since you are competing to earn the income, it would more likely be considered self-employment income, similar to if you were running a business. To have TurboTax handle it like this, you need to choose the None of these apply option on the page that says Does one of these uncommon situations apply?
On the next screen you can indicate that the work is not like your main job, then on the next screen indicate that you perform the activity in more than the current year, then your winnings will be treated like self-employment income and you can deduct your ordinary and necessary business expenses.
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