How do you track stuff that you've held for years across multiple platforms? I've got some stocks I originally bought in 2018 on Robinhood, transferred to Fidelity in 2021, and then sold this year. No idea how to verify the correct cost basis with all those moves.

You need to keep your original purchase confirmations and transfer documentation. Any time you transfer assets between brokerages, print or save PDF copies of your statements showing the cost basis information before the transfer happens. For your specific situation, log into your old Robinhood account and download your account statements from 2018 that show the original purchase prices. Even if you've closed the account, you should still have access to your tax documents for several years. Then compare those original costs with what Fidelity is reporting on your 1099-B this year. If there's a discrepancy, you'll need to manually correct it on Form 8949 when filing your taxes.

Thanks for the real-world example! Did the IRS ever question any of your trades or ask for more documentation? I'm worried about audit risk with so many transactions.

Do you need to have a separate phone for this to work, or can you deduct part of your regular personal phone? Also, how do you actually document the business use percentage?

You don't need a separate phone - you can deduct a percentage of your regular phone bill based on how much you use it for business purposes. For documenting the percentage, it's mostly about being reasonable and consistent with your estimate. I keep a simple log for a few weeks each year showing how many hours I use my phone for work versus personal use. Some people also look at their data usage from the delivery apps compared to overall usage. The key is having some method to back up your percentage if questioned, but it doesn't have to be super complicated. Just don't claim 90% business use if you're only doing deliveries part-time!

Thanks for mentioning this! I actually have bought some decent equipment - two insulated bags (around $45 total), a cup holder organizer ($20), and one of those phone mounts that clip to the air vent ($15). I didn't even think about deducting those. I'll definitely keep the receipts for all that stuff now!

Thanks for sharing your real-world experience! Do you track your inventory of supplies at all, or just expense them as you buy them throughout the year? My wife sometimes buys in bulk when there are deals.

I just expense supplies as I purchase them throughout the year, even when buying in bulk. Unless you're selling these products retail (which would make them inventory), supplies used in services are considered consumed when purchased for tax purposes. When my salon buys in bulk during sales, I still deduct it all in that tax year. The IRS understands this is normal business practice. Just keep your receipts organized in case of an audit, but don't overthink the timing of the deduction. This approach has worked for me for over 15 years without any issues.

What about things that fall into a gray area? Like those expensive brushes that last a few years but eventually wear out? Or the salon capes that might last 1-2 years? I'm never sure if those should be supplies or de minimis items.

Thanks for that suggestion! I looked into the Substantial Presence Test, but it seems that au pairs on J-1 visas are explicitly classified as "exempt individuals" for the first 2 years, meaning they don't count days toward the substantial presence test. She's definitely considered a non-resident alien for tax purposes. Really appreciate everyone's help though - I think I'm going to try one of the specialized services mentioned since the 1040NR seems to have some tricky differences from the standard forms.

Is that really necessary for au pairs? They're only here temporarily.

Yes, it applies to anyone who's required to file US taxes regardless of their visa status or how long they've been here. If they meet the $10,000 threshold in foreign accounts at any point in the year, they need to file the FBAR. Many au pairs keep savings accounts in their home countries while working in the US, and if those accounts plus any other foreign financial accounts total more than $10,000 at any point, they need to file. The penalties for not filing can be severe - starting at $10,000 for non-willful violations.

What app do you use for tracking? I've been looking for something reliable. And did you go with the 5 or 7 seat configuration? I've heard that affects whether it's considered an SUV for tax purposes.

I use MileIQ - it's been super reliable and creates reports I can send directly to my accountant. Regarding seating, I went with the 6-seat configuration (2-2-2), and yes, that helped ensure it qualified as an SUV which was important for Section 179 purposes since SUVs have higher deduction limits than passenger vehicles. The weight of the Model X also puts it in a favorable category for deduction purposes. One other tip - I took delivery in December but made sure all paperwork was completed and the vehicle was "placed in service" (used for business) before year-end. That allowed me to claim everything on that tax year rather than having to wait.

This is really smart advice. Did you have any issues with the battery range on the BMW for your typical driving?

No real issues with the battery range - the X5 hybrid gets around 30 miles of pure electric range which covers most of my in-town client visits. When I do longer trips to rural areas, it switches seamlessly to gas. Actually ended up being the perfect balance for my needs. The charging is way simpler too - I just use a regular outlet in my garage overnight rather than needing to install a special charger. Total cost of ownership has been lower than I expected when factoring in the fuel savings plus the tax benefits.