If you go the leasing route, aren't there limitations on how much of the lease payment you can deduct though? I thought I read something about "lease inclusion amounts" that reduce your deduction for expensive cars.

You're absolutely right about the lease inclusion amounts. When you lease a vehicle that exceeds certain dollar thresholds, you must add an "inclusion amount" to your income which effectively reduces your deduction. The inclusion amount varies based on the fair market value of the vehicle and when you started the lease. For 2025, the threshold where this kicks in is around $57,000. So if your luxury vehicle exceeds that amount, you'll need to calculate the inclusion amount using IRS tables and add it to your income. It's the IRS's way of creating parity between buying and leasing expensive vehicles.

Yikes, that's scary! Did you have a tax professional prepare your return or did you do it yourself? I'm wondering if having a CPA would have prevented this issue or if they sometimes suggest aggressive positions too.

Is this something a non-accountant could understand? I'm a small business owner trying to get a better grasp of tax principles but I don't have formal training in accounting or law.

Yes, a motivated non-accountant can definitely understand it. Bittker & Lokken is actually written with clarity in mind - they assume no prior knowledge of tax concepts and build up from first principles. I'd suggest starting with the chapters on gross income, then moving to deductions and credits. The book does an excellent job of explaining WHY certain tax provisions exist along with HOW they work, which makes the concepts stick better than just memorizing rules. That said, it's still a substantive text - not a quick read - but if you're genuinely interested in understanding tax law, it's worth the effort.

I used that in law school! It's a great starter book that gives you the big picture concepts. It won't make you a tax expert, but it's perfect for understanding how different pieces of the tax code fit together. The explanations are clear and they use simple examples.

Thanks for mentioning this! I didn't even think about that. I'll have to look at the paperwork I got and see if anything was withheld. Would I get all of that back if I file?

Yes, if your income is below the filing threshold and you had federal income tax withheld (box 2 on your W-2), you would get that money back when you file. However, I need to correct myself about Social Security and Medicare taxes (boxes 4 and 6) - those generally aren't refundable even if you're below the filing threshold. The employer is required to withhold those regardless of how much you make. So you won't get those specific taxes back, but any federal income tax would be refunded.

I made like $200 from DoorDash last year and didn't file anything. Should I be worried?

They are definitely operating across state lines - they fundraise online and claim to do work in at least 6 different states. That's a really helpful tip. I'll look up the charity regulators in each of those states and file complaints there too. Do you know if there's any way to coordinate these complaints so they don't just get treated as separate issues?

There's no formal mechanism for coordinating multi-state complaints, but there are a few approaches that can help. First, include in each complaint a list of all other states where you're filing, with contact information if possible. Many state regulators communicate with each other on multi-state cases. Second, there's an organization called NASCO (National Association of State Charity Officials) that facilitates coordination. You can't file directly with them, but if you mention in your complaints that the issue spans multiple states, regulators may utilize NASCO channels to coordinate. The most effective approach I've seen is to get one state really engaged first. Once one state regulator takes significant action, others typically follow suit or join forces. Focus your most detailed complaint on the state where the charity is registered or where they claim to do the most work.

The Wayback Machine is great, but also use archive.today for social media posts that the Wayback Machine might miss. I'd also suggest recording any phone calls with the charity if you're in a one-party consent state.

That's an excellent suggestion about archive.today - it's much better at capturing dynamic content like social media. About recording calls, always check your state laws first. If you're not in a one-party consent state, you can still take detailed notes during the call and immediately write down what was said afterward. Date and time stamp these notes. Courts have accepted contemporaneous notes as evidence in fraud cases when recordings weren't legally possible.

Do retirement home costs count as medical expenses for the deduction? Or only the actual healthcare portions? My grandmother is in a facility that provides both housing and nursing care, but they don't break it down on the bill.

Great question about retirement home costs. It depends on the type of care being provided. If your grandmother is in the facility primarily for medical care (like a nursing home with medical staff), then the entire cost can potentially qualify as a medical expense. However, if it's more of an assisted living situation where she has an apartment but some medical services are available, only the portion of the fee that's specifically for medical care would qualify. In that case, you should request an itemized statement from the facility that separates out the medical portion. Most reputable facilities are familiar with this request and can provide documentation for tax purposes.

I went through this last year with my father-in-law. Keep ALL receipts for everything you pay - rent, medical, utilities, food, clothing. I created a simple spreadsheet showing his monthly SS income versus all the expenses I covered. Also get a signed statement from the retirement home showing you're the one making payments. I wasn't actually audited but my return was held for review and they requested this documentation. Once I sent it all in, they processed my return with no issues. The documentation is key!