Does FreeTaxUSA handle self-employment income? I drive for Uber and do some freelance design work and always assumed I needed the more expensive software for that.

I didn't rent it out at all - purely personal use. And while I did live in it for extended periods while traveling, it wasn't my primary residence (I maintained an apartment). Does the capital gains rate depend on how long I owned it? I've had it for about 3 years now.

Since you owned it for more than a year, you'll qualify for long-term capital gains rates, which are more favorable than short-term rates (which are taxed as ordinary income). For most people, long-term capital gains rates are either 0%, 15%, or 20% depending on your income bracket. And since it wasn't your primary residence and wasn't used for income, you're dealing with a straightforward personal capital asset sale. Just remember to document all your capital improvements to maximize your basis and minimize your taxable gain.

I used TurboTax last year for a similar situation. You'll need to fill out Form 8949 and Schedule D. In TurboTax, go to the investment income section and look for "Sales of Property/Assets." Then enter it as "Other assets" rather than as a vehicle sale. Make sure you have a detailed spreadsheet of all your capital improvements with receipts backing everything up. TurboTax won't automatically know which improvements qualify, so you need to do that calculation separately and just enter the final adjusted basis.

Can EAs handle more complicated S-Corp issues though? I've heard they're good for basic tax filing but might miss some of the more strategic planning opportunities. Have you found that to be true or not?

My experience has been that good EAs are excellent at tax strategy, especially for S-Corps. Mine regularly saves me thousands through proactive planning. The key is finding someone with specific S-Corp experience - ask how many S-Corp clients they have and what industries they specialize in. What many people don't realize is that EAs often focus more narrowly on tax code than many CPAs who might divide their attention across multiple accounting services. My EA catches things my previous CPA missed specifically because taxes are her entire focus. She's particularly good at maximizing the QBI deduction and optimizing my salary-to-distribution ratio to minimize self-employment taxes while avoiding audit flags.

This is the best advice here. When I switched from a general small business CPA to one that specializes in construction companies (my industry), they found over $23,000 in deductions my previous accountant missed. Industry-specific knowledge is worth its weight in gold.

This makes a ton of sense. I'm in the tech consulting space - do you think I should be looking for someone with specific experience there? Or is S-Corp specialization more important than industry knowledge?

I just dug through my paperwork and found the engagement letter. There's a clause saying they're "not responsible for penalties or interest charged due to delays" but nothing specifically addressing refunds lost due to their negligence. Does this mean I don't have any recourse?

That clause is primarily intended to cover situations where the client provides information late or there are other factors outside the CPA's control. In your case, they had all the necessary information and explicitly confirmed they would complete the work by the deadline - then failed to do so without any valid reason. This is a clear case of professional negligence that goes beyond the scope of a standard limitation clause. The fact that they acknowledged the deadline and committed to meeting it, then simply didn't do the work, strengthens your position considerably. I would still pursue compensation despite that clause, as courts have often found that professionals cannot contract away basic duties of care and competence.

This is good advice - I went through something similar in California and was able to get penalties waived by providing emails showing my accountant had everything needed well before the deadline. I had to fill out a formal abatement request form and include my evidence.

Did she get any kind of reward money for reporting him? I heard somewhere that the IRS pays a percentage of what they collect if your tip pans out.

No, she never got any reward money because she didn't file the specific whistleblower form that's required for that program. She just wanted him to get caught, not to profit from it. From what I understand now, she could have potentially received 15-30% of whatever they collected from him if she had filed Form 211 instead of the standard reporting form. She was kicking herself when she found that out later, since he apparently had to pay back over $100k in taxes and penalties.

That seems like an ethical gray area to me. Aren't accountants required to report fraud if they know about it? Or is that just lawyers who have different reporting requirements?