That's a really good point I hadn't considered. Do you know if these church donations would still "count" somehow even if I take the standard deduction? I'm nowhere near the itemizing threshold since I rent my home and don't have many other deductions.

Unfortunately, if you take the standard deduction, you can't also claim charitable donations. That's one of the trade-offs - it's either the standard deduction OR itemizing all your qualifying expenses (including charitable donations). There was a temporary exception during COVID where people could deduct some charitable contributions even with the standard deduction (up to $300 for individuals or $600 for married filing jointly), but that provision expired after the 2021 tax year. For 2023 and 2024, we're back to the normal rules where charitable donations only help you tax-wise if you're itemizing.

Is that $500 threshold per charity or total for all charities combined? I donated clothes to Goodwill ($300ish), toys to a church program ($200), and furniture to a homeless shelter ($400) last year.

Is there any protection for whistleblowers in cases like this? I'm worried the owner would know exactly who reported him.

The IRS treats whistleblower reports as confidential and won't disclose your identity during their investigation. That said, if you're in a small business where you're the only one who knows certain details, the owner might figure it out anyway. That's why I suggested documenting your concerns in an email first and looking for another job before filing. This creates both a paper trail showing you tried to address it internally and gives you an exit strategy. The Form 3949-A can be filed anonymously if you want, though providing your contact info can help if they need clarification on anything.

Form SS-8 (Determination of Worker Status) can be filed by either the worker or the business, but in practice, it's usually filed by workers who believe they've been misclassified. As a manager without ownership, I wouldn't recommend you file these on behalf of others. If workers file SS-8 forms and the IRS determines they were misclassified, the business will need to pay both the employer and employee portions of FICA taxes (the employees can file Form 8919 to only pay their portion of FICA instead of self-employment tax).

We actually checked their credit report last week and there's nothing on it about tax liens. Does that mean the debt might be too old to collect? They haven't had any credit cards or loans during this period either, so the report is basically empty.

That's actually a potentially good sign. The IRS stopped putting tax liens on credit reports for the most part after 2018, but if this debt was active and being pursued aggressively before then, you might have expected to see something. The empty credit report aligns with their "off the grid" lifestyle, which ironically might have worked in their favor regarding the statute of limitations. However, this is still not conclusive evidence - they need to get their tax transcripts to know for certain what debts might still be collectible.

This isn't entirely accurate. If they haven't filed returns for those years, they won't meet the "return filed at least 2 years ago" requirement. The IRS also sometimes files "Substitute for Returns" which don't count as taxpayer-filed returns for bankruptcy purposes. They would need to file proper returns first.

You're absolutely right about the return filing requirement - I should have been more clear. If your friend hasn't filed returns for those tax years, they would need to file them first and then wait two years before the taxes would be eligible for discharge in bankruptcy. The Substitute for Return point is also important. If the IRS filed these on your friend's behalf, they don't count toward making the tax dischargeable - your friend would need to file their own returns to replace these.

$220 for a simple return?? That seems really expensive. Was that including state filing too?

Yes, that included both federal and state filing fees. You're right that it's not cheap - and honestly that's why I'm not going back this year. The $50 gift card was nice but when I looked at the total cost, I realized I could have done it myself for much less. I'm using one of the self-prep software options this year since my tax situation hasn't changed much. The "bonus" isn't worth the extra fees when you do the math.

Is that the same as the free version that TurboTax advertises? I tried that last year but they kept trying to upsell me and eventually said I needed to pay because of my student loan interest form.

Do you use a specific spreadsheet template for tracking? I'm wondering if I should just give up on software entirely and track everything manually from the start.

I created my own spreadsheet that specifically labels transaction types (buy, sell, short open, short close, staking reward, etc.) and calculates gains according to the actual tax rules. It was time-consuming to set up initially, but saves me headaches during tax season. I don't recommend giving up on software entirely though. I use it as a starting point and to catch transactions I might have missed, then reconcile with my own records and make manual adjustments where needed. The software is also helpful for generating the final tax forms.

Be careful with that approach. Unless you've made a formal mark-to-market election that covers your crypto trading (which is questionable since crypto isn't technically a security), you're supposed to track each transaction individually. The IRS has been increasingly focused on crypto compliance, and using an unauthorized accounting method could create problems if you're audited. They've specifically stated that cryptocurrency should be treated as property, subject to capital gains rules with specific lot identification.