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@pk  No answer from you can ever be useless. I always appreciate your expertise and your time to reply, vielen Dank! I await your colleague's response and your experience with the hypothetical scenario. Best.

To enter, edit or delete a form 1099-R - Click on Federal Taxes (Personal using Home and Business) Click on Wages and Income (Personal Income using Home and Business) Click on I'll choose what I work on (if shown) Scroll down to Retirement Plans and Social Security On IRA, 401(k), Pension Plan Withdrawals (1099-R), click the start or update button

To enter Social Security benefits reported on form SSA-1099 Click on Federal Taxes (Personal using Home and Business) Click on Wages and Income (Personal Income using Home and Business) Click on I'll choose what I work on (if shown) Scroll down to Retirement Plans and Social Security On Social Security (SSA-1099, RRB-1099), click the start or update button

Yes, the 2025 Desktop edition does require Windows 11. In addition, your system should have at least 4 GB of RAM,  1 GB of hard disk space,  and a monitor with a resolution of 1024x768 or higher.

@JulieS In situations where you sold an item on behalf of someone else, but split the proceeds with them 50/50, how would you factor that into this example? (Is that perhaps what you mean when you say "You can also add the cost of the sale to your basis."?) Thanks!    

Yes, it is entered as income on the federal tax return but not on the state tax return.  Use the Form 1099-MISC to report the income.   To enter a Form 1099-MISC that is not for self-employment - Click on Federal (Personal using Home & Business) Click on Wages & Income (Personal Income using Home & Business) Scroll down to Other Common Income On Form 1099-MISC, click the start or update button On the screen Did you get a 1099-MISC?, click on Yes On the screen Let's get the info from your 1099-MISC, enter the amount received in box 3 and continue On the screen Describe the reason for this 1099-MISC, enter a reason and Continue On the screen Does one of these uncommon situations apply? - Select None of these apply and continue On the screen Did the (reason) involve work that's like (your name) main job - Select No and continue On the screen How often did (your name) get income for (reason) - Select 2025 and continue On the screen Did the (reason) involve an intent to earn money? - Select No and continue The amount entered from the Form 1099-MISC will be entered on Schedule 1 Line 8z The total from Schedule 1 Part I Line 10 flows to Form 1040 Line 8

It depends. You may be able to deduct Medicare HMO premiums, even while working full-time, provided you itemize deductions on your federal tax return.    These premiums are considered qualified medical expenses.    However, they are only deductible to the extent that your total medical expenses for the year exceed 7.5% of your adjusted gross income (AGI).