One thing nobody's mentioned yet is that you might want to consider claiming this as a non-business bad debt if you can't fully document it as a business bad debt. Non-business bad debts are treated as short-term capital losses, which isn't as good as an ordinary business loss, but still better than nothing. For it to qualify as a business bad debt, you generally need to show you were in the business of lending money or that the loan was somehow related to your trade or business. If it was just a one-off loan, the IRS might challenge a business bad debt classification. I went through this last year with a similar amount and ended up going the non-business bad debt route because it was less documentation and less risk of audit.

Don't forget the timing issue - the bad debt deduction must be taken in the year the debt actually becomes worthless, not when you decide to write it off. If you have evidence it became worthless in 2023, you should take it then. If it's becoming worthless in 2024, take it this year. Taking it in the wrong year is a common mistake and the IRS can disallow the deduction even if you have all the right documentation. Since you filed an extension for 2024 taxes (due Oct 2024), you need to determine if the worthlessness occurred in this tax year.

One thing nobody's mentioned yet - don't just look at credentials and experience. Pay attention to how the CPA runs their business. My first CPA was super knowledgeable but his office was a disaster - lost documents, missed deadlines, slow responses. Now I have someone who might not be the absolute tax genius the first guy was, but her systems and organization are impeccable. Nothing falls through cracks. Ask potential CPAs about: - Their process for document collection - How they handle client communications - Their timeline for completing returns - What happens if there are questions after filing

I'm surprised nobody's mentioned asking about fees up front. Some CPAs charge flat rates for tax prep depending on complexity, others charge hourly. Make sure you understand their fee structure before you commit! My first CPA experience was a nightmare because they charged by the form and I ended up with a $1,200 bill I wasn't expecting.

Pro tip: Avoid MLPs in your regular brokerage account if you hate tax complications. I learned this the hard way. If you want to invest in energy stocks without the K-1 headache, look for energy companies structured as C-corps or consider ETFs that hold MLPs, as they issue 1099s instead of K-1s. Some good alternatives are tickers like XLE (Energy Select Sector SPDR Fund) or AMLP (Alerian MLP ETF) - both give you exposure to the energy sector but issue a simple 1099 instead of a K-1. Your future self will thank you next tax season!

Just a heads up that if you end up with lots of K-1s, Turbotax Deluxe won't cut it. You'll need to upgrade to Premier at minimum, and possibly Self-Employed if you have other business stuff. I found this out the hard way last year and had to pay more to upgrade mid-filing. Super annoying.

Just to add another perspective - I've been married to a Canadian citizen for 3 years who lives across the border. We initially got her an ITIN so I could file Married Filing Separately, but we discovered it was actually beneficial for us to make the election to treat her as a US resident (Form 8833) so we could file jointly. This works for us because Canada's tax treaty with the US prevents double taxation, and her Canadian income was already being taxed at a higher rate. Plus, filing jointly gave us better tax brackets and we could claim certain credits that aren't available when filing separately. Definitely worth having a tax professional review your specific situation to see which filing status is most beneficial. Each international marriage has its own unique considerations!

Has anyone successfully e-filed with a spouse who only has an ITIN? When I tried last year with my Brazilian spouse's ITIN, TurboTax kept rejecting it saying the ITIN didn't match IRS records. Ended up having to paper file which took FOREVER to process.

I'm a freelancer too and I've used both regular TurboTax and TurboTax Live. Honestly, the Live expert was totally worth it for me. I was missing so many deductions that the expert found for me - mileage I didn't realize was deductible, part of my cell phone bill, professional subscriptions, etc. They saved me at least $1,200 compared to what I would have paid doing it myself. For record keeping, start using an app like Quickbooks Self-Employed immediately - it connects to your bank/credit cards and makes categorizing expenses super easy throughout the year. Then next year your tax situation will be way cleaner.

One thing nobody has mentioned - if you're a first-time self-employed filer with complicated situations like yours, the peace of mind from TurboTax Live might be worth it just for anxiety reduction. I tried to save money doing it myself last year and ended up spending like 30+ hours still feeling unsure. This year I used TurboTax Live and the expert found SO MANY deductions I missed (especially around the home office and business percentage of things like phone/internet) and I felt confident my taxes were done right. Just make sure you get organized before the call - have all your 1099s, expense categories somewhat sorted, etc. The more prepared you are, the more value you'll get from their time.