When I bought my company car, HR gave me a fancy official bill of sale that had a separate line for sales tax. Make sure u get something like that!! Some states also have special forms for this situation. In my state they had a specific form (MV-82B I think?) that showed the tax was already paid. Without it I woulda been charged again at DMV for sure lol!

This is actually pretty standard practice when buying from a business entity, including your employer. I went through this same process when I bought a company vehicle a few years ago and was initially confused too. The key difference is that businesses are registered tax collectors with the state, so they're required to collect and remit sales tax on vehicle sales just like a dealership would. When you buy from a private party, neither you nor the seller is a registered tax collector, so you handle it at the DMV. Make sure you get a detailed bill of sale that clearly itemizes the sales tax amount, includes the vehicle VIN, and shows your company's tax ID number. This documentation will be crucial when you register the vehicle - it proves the tax was already collected and prevents double taxation. Most states have systems where this gets reported electronically, so the DMV should already know the tax was paid when you show up to register. Your $1,320 in sales tax on a $16,500 purchase sounds about right for most states (around 8% rate). Just make sure all the paperwork is properly documented and you should be good to go!

Have you considered just taking a distribution from your other business to pay for this, rather than reducing your estimated tax payments? Underpaying your estimated taxes could result in penalties and interest if you end up owing more than you paid in quarterly payments.

Before you reduce your estimated tax payments, make sure you understand the penalty implications. The IRS generally requires you to pay either 90% of the current year's tax liability or 100% of last year's tax (110% if your prior year AGI exceeded $150,000) through withholding and estimated payments to avoid underpayment penalties. If you're planning to pay $26.5k instead of $33k this quarter, you need to verify that your total payments for the year will still meet the safe harbor requirements. The underpayment penalty is calculated quarterly and can be substantial - currently around 8% annually. A safer approach might be to take a proper distribution from your other business to fund the website expense, then handle it as a capital contribution to the partnership as others have suggested. This keeps your estimated tax payments on track while still allowing you to personally fund the website expense.

Has anyone in this situation tried to coordinate with their parents to bunch medical expenses into one tax year? My mom and I are trying to plan some expensive procedures and figuring out if we should schedule everything in December or January.

This is a tricky situation that I've seen come up a lot. Since your parents paid the medical expenses directly, they're the ones who can claim the deduction - not you. The IRS is very clear that medical expenses can only be deducted by the person who actually made the payment, regardless of whose name is on the bill. However, there might be a silver lining here. If your parents provided more than half of your support for the year (which sounds possible given your work situation and the fact they paid $14,000 in medical bills), you could be considered their "qualifying relative" for medical expense purposes. This would allow them to include the medical expenses they paid for you when calculating their medical deduction. For future expenses, consider having your parents gift you the money first, then you pay the medical providers directly. This way you'd be able to claim the deduction on your return. Just make sure to document everything properly and keep records of who actually made each payment. Given your low income this year, it's definitely worth having your parents check if they can benefit from the medical expense deduction, especially if they have other medical costs that might push them over the 7.5% AGI threshold.

Has anyone here actually calculated the long-term cost of keeping a mortgage just for tax purposes? I did the math and was shocked. Let's say you have a $300k mortgage at 5% and you're in the 24% tax bracket. Your mortgage interest might save you around $3,600 in taxes in year one. But you're PAYING around $15,000 in interest that year! So you're spending $15k to save $3.6k. Even if you invest the difference and get decent returns, from a pure tax perspective, it rarely makes sense to keep a mortgage JUST for the tax deduction. The math just doesn't work out unless there are other factors at play.

This is exactly the confusion I had for years! You're absolutely right that from a pure tax perspective, keeping a mortgage rarely makes sense. The key insight that changed everything for me was understanding that the mortgage interest deduction is essentially a "discount" on your mortgage interest, not free money. If you're paying $15,000 in interest and getting back $3,600 in tax savings, you're still out $11,400. That's money you could have saved by paying off the mortgage entirely. The only time the tax math might work in your favor is if: 1) You're itemizing anyway due to other large deductions 2) You're in a very high tax bracket (35%+ marginal rate) 3) You have a newer mortgage with mostly interest payments But even then, you need to factor in the psychological benefit of being debt-free and the guaranteed "return" of your mortgage interest rate by paying it off early. I finally paid mine off last year and sleep so much better knowing I'm not hemorrhaging money to interest payments every month, regardless of what my tax software says.

So is code 201 like a yellow flag or a red flag? Kind of like when your doctor says they found something "interesting" on your test results but won't tell you what it means until you come in for another appointment? Just wondering if this is something I should be actively worried about or just waiting for their letter.

Code 201 is more of a yellow flag than a red flag - it just means they're making an adjustment and will send you a notice explaining why. I've seen this code three times over the years, and twice it was actually in my favor (they found credits I missed). The key thing is to wait for the actual notice letter, which usually arrives within 1-2 weeks of the code appearing. Don't stress too much about it - unlike some other codes that indicate holds or delays, 201 just means they're communicating with you about a change to your account. Keep checking your mailbox and you'll have your answer soon enough.