12 Thanks for the suggestion! Would I need any special documentation to prove I actually tried to collect the debt? I have the original contract, all my invoices, and email threads showing I tried to get paid multiple times.

4 Yes, documentation is critical. Keep your original contract, all invoices sent, and especially any communications showing you attempted to collect payment. Also document how you determined the company was bankrupt and the debt uncollectible - like news articles about their shutdown, bankruptcy filings, or bounced emails to company addresses. Form 8949 is typically used for capital losses, but business bad debts can sometimes be reported as short-term capital losses. However, this really depends on your specific situation and whether you're using cash or accrual accounting.

3 Good point! They definitely should have issued a 1099-NEC for payments over $600. If they didn't, you should still report the income you actually received, but that missing 1099 might be another sign the company wasn't following proper business practices.

Does Wave let you export reports that work for tax filing? That's been my biggest pain point.

Yes, you can export expense reports as PDFs or spreadsheets that work well for tax filing. The reports show all the transaction details and categories that match up with Schedule C. You can also generate specific date range reports, like quarterly or annual. The only limitation I've found is that the automatic categorization isn't always perfect, so I do have to go in and correct some entries occasionally. But for a free tool, it's pretty solid and has saved me tons of time compared to my old method of manually tracking everything in spreadsheets.

Oof that's rough. What app are you using now that has the cloud sync? I travel a lot for work and my biggest fear is losing all my trip receipts.

Is there any limit to how much you can take out after 65? And do you HAVE to take RMDs like with traditional IRAs? I'm trying to decide if I should just max my 401k or split between that and HSA.

There's no limit to how much you can withdraw after 65, and one of the best parts is that HSAs do NOT have Required Minimum Distributions (RMDs) like traditional IRAs. You can let the money grow as long as you want without being forced to withdraw it. That's why many financial planners recommend maxing out HSAs before even maxing 401(k)s beyond the employer match. The HSA is the only account that offers triple tax advantages: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. Even using it for non-medical expenses after 65, it's at least equivalent to a traditional IRA.

Your dentist unfortunately gave you incorrect information. HSA funds generally cannot be used for dental insurance premiums either, as they fall under the same restrictions as health insurance premiums. The only exceptions are the ones already mentioned (unemployment, COBRA, over 65, or long-term care). However, you CAN use HSA funds for actual dental procedures and treatments that aren't covered by insurance! So while you can't pay the premium with HSA money, you can use it for copays, deductibles, and procedures that insurance doesn't cover or only partially covers.

Great point about state taxes. Do K-1 losses always work the same way for state taxes as they do for federal? I'm in Virginia and sometimes our state rules are different than federal.

State tax treatment generally follows federal rules, but there can definitely be differences. Virginia typically conforms to federal tax law for pass-through entities like partnerships, so your K-1 loss should flow through to your state return similarly. However, some states have their own limitations or adjustments for passive losses. The best approach is to check your specific state's tax department website or consult with a tax professional familiar with your state. Even with potential variations, in most cases you'll still see some benefit at the state level from reporting your K-1 loss.

How much was the penalty? I'm wondering because I might have done the same thing last year... thought my K-1 loss was so small it wouldn't matter 😬

These volunteer programs are hit or miss for investment questions though. I tried VITA last year and the volunteer wasn't comfortable answering my stock trading questions. Said they mostly handle basic returns without investment income.