How exactly does the home office deduction work for something like this? Like if someone uses their home office for preparing presentations but it's not their main job, can they still claim it?

The home office deduction can apply even for part-time self-employment activities. The key requirements are that the space must be used exclusively and regularly for business purposes. "Exclusively" means the area is used only for business activities (not also as a guest bedroom or family TV room). "Regularly" means it's used on an ongoing basis for business, not just occasionally. For someone preparing presentations, if they have a dedicated desk or room where they exclusively work on these business activities, they could potentially claim the deduction. They would calculate the percentage of home used for business (square footage of office ÷ total home square footage) and apply that percentage to eligible home expenses (rent/mortgage interest, utilities, insurance, etc.) or use the simplified method ($5 per square foot up to 300 square feet).

This is actually really helpful to know! I've been stressing about picking the exact right business code for my freelance graphic design work.

Do they handle both the 5498-SA and 1099-SA forms? I have both because I contributed to my HSA and took distributions in the same year.

Yes, they handle both forms. The 5498-SA (which shows your contributions) and the 1099-SA (which shows distributions) are both covered in their free federal filing. They use Form 8889 to reconcile everything related to your HSA. You'll see a specific section for HSA accounts where you can enter both your contributions and distributions. Just make sure you have your 1099-SA handy to enter the distribution amount and the correct box number (usually Box 1 shows total distributions, and Box 2 shows earnings on excess contributions if applicable).

Ouch! Did you have to pay a lot? I'm paranoid about this because I used my HSA card at a pharmacy where I bought both prescription meds and some other non-medical stuff on the same transaction.

That's a great point about documentation - I hadn't considered how much more scrutiny a luxury vehicle might get. Do you think it matters if I use actual expenses vs. standard mileage rate when it comes to audit risk? And were there specific record-keeping issues the IRS focused on during your audit?

In my experience, using actual expenses (like you'd need to do for depreciation) definitely increased the scrutiny compared to standard mileage rate. The IRS agent specifically told me that luxury vehicles using actual expense method are flagged more frequently. During the audit, they focused heavily on three things: 1) Contemporaneous mileage logs (they wanted to see that I recorded trips when they happened, not recreated later), 2) Documentation of business purpose for each trip, and 3) Evidence that I had another vehicle for personal use. They were very skeptical of my claim that the Mercedes was 100% business when I didn't have another car in my name. My advice: keep a dedicated app or logbook in the car, document every single business trip with purpose and mileage, take periodic odometer photos, and keep all maintenance records showing the mileage progression. If you're claiming 100% business use, they'll want to see how you handle personal transportation.

Those limits seem low - is that for all vehicles or just luxury ones? I thought there were special rules for trucks and SUVs that let you deduct a lot more.

Does this apply even if you use one of those tax relief companies that advertise on radio? They always claim they can settle for "pennies on the dollar" but I assume that's just marketing hype?

Those "pennies on the dollar" claims are extremely misleading. What those companies are referring to is the IRS Offer in Compromise program, which is only available in very specific hardship situations where you genuinely cannot pay your tax debt. You have to prove significant financial hardship, and most people who apply get rejected. Those companies charge thousands in fees for something you can do yourself, and they often make promises they can't keep. They can't get any better deal from the IRS than you can get yourself. And yes, even with an accepted Offer in Compromise, the IRS will still apply interest to your original tax debt before determining your settlement amount.

Did you have to fill out any special forms for the penalty abatement? Or was it just handled over the phone?

For donor-advised funds, is there a minimum amount that makes sense to start with? And do you recommend any particular providers?

Most major investment firms like Fidelity, Vanguard, and Schwab offer donor-advised funds with minimums around $5,000 to open and $500-1,000 for additional contributions. I personally use Fidelity Charitable because their platform is user-friendly and their fees are reasonable. The amount that "makes sense" depends on your tax situation, but generally, it's most beneficial when you're bunching multiple years of charitable contributions into a single tax year to exceed the standard deduction threshold. For someone at your income level, contributing $10,000+ would typically provide meaningful tax benefits, especially if you're already itemizing deductions.

I'm a physician who went the real estate route. The tax benefits are real - depreciation, mortgage interest, and expense deductions. But be cautious about passive losses - at your income level, you may not be able to deduct those against your W2 income unless you qualify as a real estate professional (which is tough with a full-time medical career). Consider syndications or REITs if you want the benefits without active management. Just do your due diligence - there are many questionable deals out there.

Thanks for the insight! I was worried about the time commitment. REITs sound more my speed since I barely have time for hobbies as it is. Any particular types of REITs you'd recommend looking into first?