Shoot I didn't even think about that! I was planning to go with Schwab. Does anyone know how long they typically take to process?

With Schwab, you're cutting it close but might still be okay. Last I checked, they can typically establish a solo 401k within 1-2 business days if all your paperwork is complete and accurate. I'd recommend calling them directly ASAP though - their customer service can tell you exactly what you need and might even be able to expedite the process if you explain the deadline situation. One important thing: make sure you have your EIN ready! If you don't already have an Employer Identification Number from the IRS for your business, you'll need that before opening a solo 401k. That's another process that could add time.

This is great information but I'm still a bit confused. So if I just get the paperwork submitted tonight, I'm good? And then I can actually fund it later? Does the solo 401k need to be with the same bank where I have my business checking account?

Does this Section 382 stuff apply to all business types or just C-corps? I've got an S-corp with some losses and am thinking about bringing in a partner next year. Would that trigger these limitations?

Section 382 primarily applies to C corporations, not pass-through entities like S corporations where losses generally flow through to shareholders. However, S corporations that were previously C corporations and are carrying C corporation NOLs would still be subject to these limitations. For your S-corp situation, adding a partner wouldn't trigger Section 382, but it could affect how losses are allocated among shareholders. When ownership percentages change in an S-corp, it can affect the allocation of losses based on each shareholder's basis and the number of days in the tax year that each ownership percentage was in effect. Different rules apply, but you should definitely consult with a tax professional before adding that partner.

You're absolutely right. I appreciate all the advice here, but I think I do need professional help with this. Does anyone have recommendations for how to find a tax attorney who specifically specializes in business losses and NOLs? Is there a particular certification or background I should look for?

Look for a tax attorney who is also a CPA - that combination is powerful for complex business tax issues. I'd specifically ask potential attorneys about their experience with NOL monetization strategies and business restructuring for tax purposes. The best ones will typically have backgrounds working at either the IRS, major accounting firms in their business tax departments, or law firms with dedicated tax practices. You want someone who has actually handled similar situations, not just someone who understands the general tax code.

I've heard about the Offer in Compromise but don't think we'd qualify since we both have stable jobs. We're not destitute, just don't have $7k liquid cash sitting around. Do you know if they ever offer compromises for people with regular incomes who just can't pay a large lump sum?

You're right that OIC is tough to get with stable income. It's usually for people with serious financial hardship where they'll likely never be able to pay. For your situation, a payment plan is probably more realistic. If the lump sum is the issue but you could manage it over time, definitely go with the installment agreement. Pro tip: if you can pay it off within 180 days, you can set up a short-term payment plan with no setup fee at all. Otherwise, the long-term plans have reasonable monthly minimums based on how much you owe.

This is really good advice. The IRS has a Tax Withholding Estimator on their website that's much more accurate than the worksheet. It lets you put in both spouses' income and gives you the exact dollar amount to put on line 4(c) for extra withholding.

Which tax software gives the most detailed tracking? I used FreeTaxUSA this year and their tracking doesn't seem to have any more info than the IRS site.

In my experience, TurboTax and H&R Block tend to have the most detailed tracking features built into their apps and websites. They pull data from the IRS but present it in a more user-friendly format with better explanations. FreeTaxUSA is great for filing affordably, but their after-filing support isn't as robust as the premium services. TaxAct falls somewhere in the middle - better tracking than FreeTaxUSA but not quite as comprehensive as TurboTax.

That's actually reassuring! Did you do anything special to get your refund moving or did it just suddenly appear one day? I'm hoping mine moves along without me having to do anything.

Thanks for bringing this up! I checked my lease and surprisingly, subletting is allowed with landlord approval. My city also allows short-term rentals with proper registration. This is super helpful though - I wouldn't have thought about checking local regulations beyond just my lease.

Wait, aren't you technically running a business though? Could you have classified it as self-employment instead of rental activity? Then maybe the losses would apply differently?

I asked my accountant about that too! She said it depends on the level of services provided. If you're just providing basic rental amenities (bed, bathroom, etc.), it's still rental activity. If you're providing substantial services like daily cleaning, meals, concierge services, etc. - more like a B&B - then it might qualify as a business rather than rental activity. In my case, I wasn't providing those "substantial services" so it still counted as rental activity with all the passive loss limitations.