14 What if I didn't officially claim the car for business use but I did use it sometimes for side gig deliveries? Do I still need to worry about this depreciation thing?

7 If you never claimed the car as a business expense on your tax returns, then you don't have to worry about depreciation recapture. The concern only applies if you took actual tax deductions for business use of the vehicle in prior years. However, if you did use it for your side gig but never claimed the deductions you were entitled to, that's a different issue - you missed out on potential tax savings in previous years, but it won't affect how you report the sale now. You'd simply use your original purchase price as your basis (minus any depreciation you actually claimed on tax returns, which in your case sounds like zero).

11 Technically, all capital gains should be reported regardless of size. But in reality, the IRS has bigger fish to fry than a $250 gain on a personal vehicle. Most people don't even report personal vehicle sales unless they're significant gains.

What's the link to that pre-qualifier tool? I can't find it on the IRS site and their search function is terrible.

Here's the link to the IRS pre-qualifier tool: https://irs.treasury.gov/oic_pre_qualifier/. It's definitely not easy to find on their site! The tool walks you through a series of questions about your financial situation to help determine if an Offer in Compromise might be right for you. It's not a guarantee, but it's a good starting point before you invest time in the full application.

Does that compliance requirement also apply to payment plans or just OICs?

Payment plans (installment agreements) also have compliance requirements, but they're typically not as strict as the 5-year requirement for an Offer in Compromise. With a payment plan, you generally need to file on time and pay on time while the agreement is in effect. If you default on a payment plan by missing payments or failing to file future returns, the IRS can terminate your agreement and may resume collection actions. They're sometimes willing to reinstate agreements if you quickly get back into compliance, but it's best not to test their patience.

How long did it take you to complete your return with the self-employment stuff? I'm trying to budget my time and wondering if I should just block off an entire weekend.

It took me about 4-5 hours total, but that was spread over two evenings. The self-employment section definitely takes the most time, especially the first year when you're learning what expenses qualify and gathering all your receipts and documentation. I'd recommend setting aside at least a half-day of uninterrupted time, and make sure you have all your documents organized before you start. Have a folder with all your receipts for business expenses, home office measurements, mortgage documents, etc. Being organized upfront saves tons of time during the actual filing process.

This is great advice! Do you just find a random CPA or are there ones that specialize in self-employment situations? I'm worried I'll end up with someone who just plugs numbers into software like I could do myself.

Does anyone know how much the student visa renewal typically costs? And do international students get any discounts on banking services? I'm planning my budget for next semester.

Student visa renewal costs around 1,100-1,500 AED (roughly $300-400 USD) depending on the emirate and institution. This typically includes the visa fee, medical examination, and Emirates ID card. For banking, several UAE banks offer student accounts with reduced or waived fees. Emirates NBD and ADCB have specific student packages with no minimum balance requirements and free international transfers to certain countries. Some universities also have partnerships with specific banks that provide additional benefits to their students. Check with your institution as they might have recommendations based on existing relationships.

Does everyone know if there's a good resource to check these agreements? I'm from South Africa and not sure where to look for this info.

Oh crap, I didn't even think about state taxes. I lived in Illinois for two of those years and New York for part of another before moving abroad. Are the processes similar for catching up on state taxes? Do I need to file state returns before federal?

The processes are similar but each state has its own forms and procedures. Illinois and New York both have relatively straightforward processes for filing past-due returns, but they'll have different forms than what you're filing federally. Both states maintain prior year forms on their tax department websites. You don't necessarily need to file state before federal - you can work on them simultaneously. However, since most state returns start with your federal AGI or taxable income, it often makes practical sense to complete your federal return first. Just be aware that both states may have their own penalties and interest for late filing, separate from the IRS penalties. New York in particular can be quite aggressive with penalties, so don't delay getting those filed once you start the process.

This! The FBAR penalties are no joke. My cousin got hit with a $10,000 penalty for a non-willful violation. If they determine it was willful, penalties can go up to $100,000 or 50% of the account balance. Definitely something to take seriously!