Thank you for this advice! Did you find it difficult to verify if a CPA truly had expertise with multi-state returns? I'm worried about just taking someone's word for it and then finding out they weren't as experienced as they claimed.

That's a valid concern! I'd recommend asking potential CPAs specific questions about your situation before hiring them. Ask how many multi-state returns they handle annually and specifically about rental property scenarios similar to yours. An experienced CPA should be able to immediately discuss specific forms (Schedule E, part-year resident forms) and potential pitfalls without hesitation. Also, don't just go with someone who says "yes, I can do that" - ask them to explain HOW they would approach your specific situation. A truly experienced multi-state CPA will mention things like sourcing rules, reciprocity between states, and credit for taxes paid to another state. If they can't speak to these specifics, that's a red flag.

Did your CPA handle everything remotely or did you have to go into their office? I'm in a similar situation but travel a lot for work so in-person meetings are tough.

I hadn't thought about coworking spaces! That's a really smart alternative. Do you know if there are any specific documentation requirements for using coworking spaces as a business expense? And would that still work if I keep the hotel for personal comfort but also use a coworking space?

For coworking spaces, keep the receipts/invoices from the space and note the business activities performed there each day. Take photos of your workspace and save any digital check-ins. If you're producing deliverables while there, note that in your records. You could absolutely still keep the hotel for personal reasons while using a coworking space for business. This actually creates a much cleaner deduction situation because the coworking space has no personal use component - it's 100% business. The hotel would then be clearly personal and non-deductible, but your dedicated workspace would be fully deductible. This arrangement also makes it much harder for the IRS to question the business purpose since there's no mixing of personal and business use in the same space.

Going through an audit sounds terrifying. Did you end up owing a lot more in taxes after they disallowed your deductions?

That's a good point I hadn't considered. I think each employer is definitely calculating as if that's our only income. How would I figure out what the right additional withholding amount should be for each job? Is there a calculator for that?

The IRS has a Tax Withholding Estimator tool on their website that's designed exactly for situations like yours with multiple jobs. It will walk you through entering info from all four W-2s and then recommend specific withholding amounts for each job. For a quick rule of thumb, take your total expected annual tax bill (probably around $44-45k based on your income) and subtract what you're currently having withheld. Then divide that shortage by the number of pay periods remaining in the year to determine how much additional withholding you need across all jobs. You can split that amount across all four jobs however makes sense for your cash flow.

At their income level ($270k), they're probably phased out of most credits. The Saver's Credit phases out at $73k for married filing jointly, and the Child Tax Credit starts phasing out at $200k. Education credits have similar income limitations.

But this seems super unfair to people barely getting by. So the tax code basically says "ur so poor u dont owe taxes... unless ur self employed then pay up"?? Is there any way around this or any special credits for low income self employed people?

You make a good point about the seeming unfairness. There are actually some options that can help. You may qualify for the Earned Income Tax Credit (EITC) which is specifically designed for lower-income workers, including self-employed people. This credit is refundable, meaning you can get money back even if you don't owe income tax. Also, don't forget about business deductions. You can deduct legitimate business expenses from your self-employment income before calculating the 15.3% tax. This includes things like supplies, mileage, home office expenses, phone/internet costs used for business, etc. For many gig workers, these deductions can significantly reduce the taxable self-employment income, sometimes by 30-50% depending on your situation.

TurboTax does handle this correctly. I was in this situation and it asked if I had any self-employment income. When I entered my DoorDash earnings, it automatically added Schedule C and SE to my return. It also walked me through possible deductions like mileage and phone expenses that helped lower the self-employment tax I owed.

Thank you so much for this confirmation. I'm definitely going to find a new tax preparer. Quick follow-up - if I claim the standard mileage deduction, can I still deduct the cost of the new tires separately or is that considered included in the mileage rate?

If you use the standard mileage rate (which is typically the better option with high mileage like yours), that rate is designed to cover all costs of operating your vehicle including depreciation, maintenance, repairs, tires, gas, oil, and insurance. So no, you cannot separately deduct the cost of tires in addition to taking the standard mileage rate. However, you can still deduct other legitimate business expenses that aren't related to your vehicle operation, such as business supplies, a portion of your cell phone bill if used for business, business insurance, or any other ordinary and necessary business expenses.

I used TurboTax Self-Employed for a similar situation last year. When you get to the 1099-MISC section, just enter the information exactly as it appears on your form. Then when it asks about your business, create a Schedule C for your personal assistant business, and TurboTax will guide you through entering all your expenses including mileage. It worked perfectly - just make sure you choose the Self-Employed version not the cheaper ones.