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.

11 Does exclusive business use mean I can't ever let my kids do homework in there or have guests use it when they visit? What about if I occasionally take personal calls in the space? The IRS can't possibly monitor how I use every room, right?

21 The exclusive use requirement is quite strict. Your kids doing homework there, guests using the space, or taking personal calls would all technically violate the exclusive business use requirement. No, the IRS doesn't have cameras in your home, but if you're audited, they may ask detailed questions about how the space is used, request photographs, or even visit the location. They look for things like children's toys, guest beds, or other indicators of personal use. Many taxpayers have lost their entire home office deduction because they couldn't prove exclusive business use. It's not worth risking a potentially large deduction over occasional personal use, especially with a dedicated construction project specifically for business purposes.

1 I did look into renting, but where I live, commercial space is ridiculously expensive. Even a tiny office would cost me about $3,000/month. The construction is around $42,000 total, so it pays for itself pretty quickly compared to renting. Plus, I love working from home and not having to commute. The depreciation and potential recapture issues are definitely something I need to consider though. I just want to make sure I'm taking advantage of all possible tax benefits since this will be 100% business use.

This is good advice. Financial aid offices deal with this kind of thing all the time. My son's college accepted a signed statement explaining why we couldn't provide the exact document they requested, along with the tax transcript showing the amended information.

Thanks for the advice! One question - if I pay online now before filing, how do I make sure the payment gets matched to my return when I eventually mail it?

When you make a payment through the IRS Direct Pay system, you'll select the reason for payment (in your case "extension" or "tax return"), the tax year (2022), and provide your identifying information like SSN. The IRS will automatically match your payment to your return when it's processed based on this information. Make sure to print the confirmation page after making your payment and keep it with your tax records. If there's ever a question, this confirmation serves as proof that you paid on time, even if your return is processed later.

The Non-Filer tool is actually designed for people who aren't required to file a return but need to register for specific benefits or credits. It's not appropriate for someone who has a regular tax filing obligation like the OP who has already prepared their return. Using the Non-Filer tool when you actually should be filing a complete tax return can create complications in the IRS system and potentially flag your account. The OP should either mail their completed return or work with a tax professional to efile it.