One thing nobody mentioned yet - you should also check if any of these artists are in countries with tax treaties with the US. Some countries have specific rules about how commissions are handled. For example, I work with artists in Canada and there's different documentation requirements than for artists in, say, Brazil.

I messed up this exact situation last year and got hit with a CP2000 notice. Make SURE you keep proof of payments and all communications with these artists. The IRS flagged my contractor payments because I couldn't prove some were to foreign individuals. Even if you can't get W-8BENs from everyone, save emails, payment receipts, anything showing they're international.

Something important to consider that nobody has mentioned yet: make sure that loan was actually made with the expectation of repayment. The IRS looks at whether you had a reasonable expectation of being paid back when you made the loan. If they determine you never really expected to get paid back (like if your friend had terrible credit or no income), they might classify it as a gift rather than a loan that went bad. Also, keep in mind that nonbusiness bad debts are treated as short-term capital losses even if the loan was for more than a year. This means you're limited to offsetting capital gains plus up to $3,000 of ordinary income per year. If your loss is bigger than that, you'll carry the remainder forward to future tax years.

I went through almost the identical situation last year with a cousin. Loaned $6,500, got back $2,000, and then nothing despite dozens of texts and calls. I claimed the bad debt deduction and it did work, but here's a tip: document EVERYTHING. I made a simple timeline of all attempts to collect (with screenshots of texts and emails). Also, I did send a certified demand letter as a final step which helped prove I made reasonable collection efforts. The tax software I was using (TurboTax) actually had a specific section for bad debts under capital losses. My refund went through without any issues, but I've heard these deductions can sometimes trigger additional review, so having good documentation ready is important.

If you have a Traditional or Roth IRA, you can sometimes make tax payments through the same investment firm for free. I use Fidelity and they let me make federal and state estimated tax payments with no fees.

Don't forget to account for the safe harbor rules when making estimated tax payments! As long as you pay either 100% of last year's tax liability (110% if your AGI was over $150,000) or 90% of your current year's liability, you won't face underpayment penalties even if you end up owing more. This was a lifesaver for me because my income fluctuates a lot month to month as a contractor, so calculating exact quarterly estimates was driving me crazy.

Quick tip about Form 8863 that helped me: keep ALL your receipts for education expenses, not just tuition. Things like required books, supplies, and equipment can count as qualified education expenses even if they don't show up on your 1098-T. For my nursing program, I was able to claim about $1,200 in additional expenses for required clinical supplies that weren't billed through my school. This significantly increased my education credit! Just make sure they're required for enrollment or attendance in your courses.

I'm late to this thread but wanted to add that the timing of when you claim education credits can make a huge difference financially. If your income is going to change significantly between tax years, you might want to try to bunch your education payments. For example, if you expect to make a lot less money next year, try to defer paying for spring classes until January if possible. Education credits are more valuable in years when your income is lower (but still high enough to have tax liability).

I'm a bookkeeper for several small businesses, and I've seen the full spectrum of ERC situations. Some of my clients qualified legitimately (significant revenue drops in 2020-2021), while others were talked into applying by these aggressive ERC firms despite clearly not meeting the criteria. The most important thing to understand is that the IRS isn't stopping ERC processing to reject everyone - they're implementing better fraud detection. If you legitimately qualified and have proper documentation, you'll likely be fine even with the increased scrutiny. Red flags I've seen in problematic claims: - Claiming qualification despite stable or increased revenue - Stretching "partial suspension" to include minor operational changes - No documentation connecting government orders to specific business impacts - Using ERC mills that take percentage-based fees - Claims that seem copy-pasted rather than specific to your business

Has anyone tried reaching out to their ERC provider to get clarification on their qualification? I've been calling mine for three weeks with no response. Their website is now "under maintenance" and their office line goes straight to voicemail. I'm starting to think they've disappeared completely now that the IRS is cracking down. We paid them $12,000 upfront (they promised it was "safer" than percentage-based fees) and now I'm worried they just took our money knowing we wouldn't qualify.