I just looked it up and unfortunately my state isn't included in the Direct File pilot program yet. Seems like it could be a good option in the future though! I'll probably go with one of the free alternatives mentioned here instead of paying for TurboTax.

Is FreeTaxUSA actually reliable? I'm always worried about using less well-known tax software. Do they have good support if you have questions?

Does the standard mileage rate usually work out better than tracking actual expenses? My car is pretty old and fuel efficient but I'm driving a TON for deliveries.

In my experience, standard mileage usually works out better for newer cars or fuel-efficient vehicles. I drive about 25,000 miles a year for deliveries in a 2018 Corolla, and the standard deduction gives me around $16,000+ in deductions which is way more than I'd get itemizing. For older vehicles that might need more repairs or gas guzzlers, tracking actual expenses could potentially be better. The key is to try calculating both ways for a month and see which gives you the bigger deduction. Just remember if you choose actual expenses in the first year, you're generally stuck with that method for the life of that vehicle.

This is actually a really good point. I worked in insurance for years and this arrangement could potentially void the insurance coverage entirely. Most policies require that the regular drivers be listed, and if there's a claim and they discover misrepresentation, they can deny everything.

Thanks for bringing this up! We're in Pennsylvania, which isn't a community property state. Do you know if there are any specific state-level considerations for non-community property states that might affect our decision?

For non-community property states like Pennsylvania, you generally report income and deductions based on which spouse actually earned the income or paid the expense, which is much simpler. The main state-level consideration would be your state tax rules around dependent exemptions or credits. Some states have their own child tax credits or dependent exemptions that might have different phase-out thresholds than the federal ones. Pennsylvania specifically has a relatively simple income tax system with a flat rate, but you should check if there are any dependent-related benefits at the state level that might influence your decision about who claims your daughter.

The Earned Income Tax Credit isn't available for married filing separately status - it's one of the credits you give up when you choose MFS. They'd need to file jointly to claim it, which defeats the purpose of keeping the student loan payments lower.

Does Section 179 still apply with the luxury auto limits though? I thought those kicked in regardless of whether you use 179 or regular depreciation.

You're absolutely right about the luxury auto limits - they do still apply even with Section 179 deductions. So there's a cap on how much you can deduct each year regardless of which method you choose. What's important to note is that with Section 179, you can deduct a larger amount in the first year rather than spreading it out over several years with regular depreciation. But as you mentioned, there are still annual limits for passenger vehicles regardless of which method you use. For 2025, those limits are pretty restrictive for higher-end vehicles, which is something to seriously consider when making this purchase.

This is really good advice. My brother put his lawn care company logo on his truck and then got into a minor fender bender. Insurance company gave him trouble because he hadn't disclosed it was being used for business purposes. Cost him a ton in the end.

Careful with the cashless exercise suggestion - that only works if the company is publicly traded or has some kind of secondary market for the shares. Sounds like OP's company is still private with no immediate IPO plans.

Good point about the cashless exercise - I was assuming there might be a secondary market since it's a Series D company, but you're right that it's not guaranteed. Another option to consider is a net exercise if the company allows it. With a net exercise, you surrender some of your options to cover the exercise cost, so you get fewer shares but don't have to put up any cash. Won't help with the tax withholding for NSOs though.

I've had good luck with The Startup CPA (thinkthis.com). Not cheap but they actually understand equity compensation and saved me a ton on AMT planning. Worth the fee considering how much is at stake with these decisions.