No way! I paper filed in February and I'm STILL waiting for my refund. The IRS is a disaster right now. E-file if you possibly can.

Do you know roughly what CPAs are charging for a return with Form 8915-e? I'm trying to decide if it's worth it vs waiting for my regular software to update.

I hadn't heard of this program. Would this still apply even though he passed away? And how did you handle estimating income when there were no clear records?

Yes, it still applies for deceased taxpayers when the estate representative initiates the disclosure. The program essentially acknowledges that you're coming forward voluntarily before any IRS enforcement action. For estimating income, we used industry standard profit margins for his type of business, looked at his living expenses and assets acquired during those years, and made reasonable estimates. We documented our methodology carefully and explained the cash-only nature of his business. The IRS was actually surprisingly reasonable once they understood we were making a good faith effort. For some years, we used Form 8275 (Disclosure Statement) to explain our estimation methods. The key was being transparent about how we arrived at the figures rather than just putting random numbers.

He did own his house - bought it in the late 90s and paid it off around 2003 according to what he told me. But I can't find any mortgage paperwork. That's a good idea about property records though, I should check with the county assessor's office to see what they have. That might at least give me some baseline for what he was earning back when he qualified for the mortgage.

We have an HDHP with an HSA that we max out, but I'm confused about how the employer stipend affects the Premium Tax Credit. Our plan isn't through the marketplace - does that automatically disqualify us?

Yes, that's a key point I should have clarified - to qualify for the Premium Tax Credit, you must purchase your health insurance through the Health Insurance Marketplace (Healthcare.gov or your state's exchange). If you bought your insurance privately outside the marketplace, you won't be eligible for the Premium Tax Credit regardless of your income. For your HSA, you're making a smart move by maxing it out! The stipend doesn't affect your HSA contribution limits at all. You'll still get the full tax deduction for your HSA contributions even while receiving the stipend, which is one of the few "double benefits" allowed in the tax code.

I used TurboTax last year with a similar situation. It did ask about health insurance and whether I received any stipends, but I found it confusing. I had to manually make sure the stipend was included as income (mine was on my W-2 already). The medical expense deduction part worked fine though - it walked through itemizing and the 7.5% AGI threshold clearly.

I tried freetaxusa instead of TT and it handled my health insurance stipend situation perfectly. It specifically asked if I received any benefits for health insurance and guided me through reporting it correctly. Much cheaper than TT too!

Does the software handle the reasonable compensation requirements and QBI calculations properly? I tried doing my own S Corp return once and ended up with a notice from the IRS about my salary being too low relative to distributions. Cost me way more than what I saved on preparation.

The software does have warnings about reasonable compensation if your salary seems too low compared to distributions, but it doesn't give specific guidance on what's "reasonable" - that's still on you to research and determine. For QBI, it does the calculations automatically once you enter all the required information. The wizard asks you questions about your business type and aggregation elections to determine eligibility. It's actually handled really well. You're right that getting those aspects wrong can be costly - I spent extra time researching those specific areas before filing. There are also some good YouTube tutorials specifically on S Corp tax prep using the major software packages that helped me avoid common mistakes.

That makes a lot of sense about the experience levels. I think I'm actually going to look into a local firm based on your suggestion. I'm realizing now I've been evaluating purely on price rather than value. I don't mind paying the same amount if I'm getting actual business advice along with the tax prep. Do you think it's too late to switch for this tax season, or should I wait until next year?

No kids unfortunately. It was just me and my ex-wife. We don't have any dependents together, and no one else lived with us. Based on what everyone's saying, looks like I'm stuck with the Single filing status and this huge tax bill. Just wish I'd known about this earlier in the year so I could have adjusted my withholdings.

That's tough, sorry to hear it. Without a qualifying dependent, you're right that Single is your only option. For next year, definitely update your W-4 with your employer ASAP to avoid withholding problems. One thing to consider is whether you might qualify for any tax credits based on your situation. The Saver's Credit could apply if you contributed to retirement accounts and your income isn't too high. There might also be education credits if you paid any tuition or student loan interest.

This is good advice. Also, don't forget about any legal fees specifically related to tax advice during your divorce. Those might be deductible too, even though general divorce attorney fees aren't. My accountant helped me identify about $1,800 in deductible legal fees from my divorce last year that were specifically for tax consultation.