Thanks for your expertise! The thing is, we received a "paid in full" letter from the mortgage company in September, so I assumed everything was completely squared away. Could there still be fees even after receiving that kind of letter? And if so, would those fees have affected the house sale?

If you received a "paid in full" letter, then the loan was definitely satisfied from the mortgage company's perspective. The discrepancy is almost certainly just a reporting error in their system. The sale of the house wouldn't have been affected because the mortgage lien would have been removed from the property once the loan was paid off. That's why you were able to sell without issues. For tax purposes, you should keep that "paid in full" letter with your dad's tax documents as proof that the OMP figure on the 1098 is incorrect. The mortgage interest amount on the 1098 should still be accurate and can be deducted on his final return for the portion of the year before he passed away.

For a deceased taxpayer, you'd report all the mortgage interest paid during the period they were alive on their final tax return. You don't need to prorate the amount shown on the 1098 - just report whatever interest was actually paid before their death. The 1098 should show the total interest paid for the year up to the date of payoff or through December if the mortgage continued.

Any specific QuickBooks version you'd recommend? I've heard there are different options and I'm not sure which would be best for a small S-Corp with just me as the only employee right now.

I'd recommend QuickBooks Online Plus for S-Corps rather than the Self-Employed version. The Self-Employed version is great for simple sole proprietorships but doesn't handle the complexity of S-Corps well. The Plus version lets you track inventory if needed and has better reporting features for corporations. Most importantly, the Plus version connects with payroll services which you absolutely need as an S-Corp owner to properly pay yourself that required "reasonable salary" through W-2 payroll. I use QuickBooks Payroll alongside it which automatically calculates all the withholding and generates the quarterly 941s and annual W-2/W-3 forms. Trust me, trying to handle S-Corp payroll manually is a nightmare you don't want!

Same experience here. The business version of TurboTax doesn't explain the specific S-Corp requirements very well. I missed the whole thing about needing to file Form 1120-S by March 15th (NOT April 15th like personal returns) and got hit with penalties. Now I just hand everything to my accountant and it's worth every penny.

That should be illegal though, right? They can't advertise a guarantee prominently and then hide in fine print that it doesn't apply to their main product that most people use?

I used it this year! It's definitely more basic than TurboTax but gets the job done. The interface isn't as polished but I saved like $120 and my refund was exactly the same as what TurboTax calculated when I did a comparison before submitting. Only downside is they don't support some more complex tax situations like multi-state filing or foreign income.

Would it help if my friend kept his own detailed records of all payments? Like copies of check deposits, bank statements, etc? Or does the Social Security Administration only count "official" earnings reported on tax forms?

The Social Security Administration primarily relies on official earnings reported to them through the tax system. Your friend's own records might help in an audit situation, but they don't automatically get credited to his lifetime earnings record for Social Security purposes. That's why it's so important to either get the proper documentation from employers or file forms like the SS-8 (to determine worker classification) or 8919 (to report wages when your employer didn't issue a W-2). These create official records that the SSA will recognize when calculating future benefits.

This is exactly what happened to my wife. She was a "nanny" for a family for 3 years, no 1099s, paid in cash. After we talked to a tax person, turned out she should have been classified as a household employee all along! The family owed back employment taxes.

Does the size of the portable building matter? I'm looking at something smaller (8x12) for my business. Would that have a better chance of qualifying for Section 179 since it's obviously more "portable" than larger structures?

Size can certainly help strengthen your case. An 8x12 structure is clearly more portable than larger buildings, making it easier to argue it's personal property rather than a real estate improvement. Smaller buildings are also more likely to be sold in the marketplace as movable units rather than permanent structures. However, the fundamental criteria remain the same regardless of size - lack of permanent foundation, designed to be relocated, not permanently affixed to land, etc. Even large portable buildings can qualify if they meet these criteria. The key is always proper documentation of the portable nature and 100% business use.

Did you have to file any special forms beyond the regular Section 179 form? And did you classify it as "furniture and equipment" or something else in your tax software?

No special forms were needed beyond Form 4562 (Depreciation and Amortization) where you claim Section 179 deductions. I listed it as "Portable Workshop Structure" in the property description. In terms of classification, my accountant put it under "Machinery and Equipment" rather than anything related to real estate or buildings. She said this classification further reinforces that it's personal property eligible for Section 179 rather than a building improvement that would need to be depreciated over a longer period.