Thank you for the suggestion! I definitely don't want to do anything illegal. Would these credits help even if he doesn't make much money? He works part time and gets some cash jobs on the side (probably doesn't report all of that income).

Yes, these credits can definitely help people with lower incomes! The Earned Income Tax Credit (EITC) is specifically designed for lower-income workers and is refundable, meaning he could get money back even if he owes no tax. Regarding the unreported cash income - that's a separate issue, but he should know that claiming tax credits while not reporting all income could create problems if he's audited. The safest path is to report all income and claim the credits he's legally entitled to.

No, if he doesn't claim his daughter as a dependent, he can't file as head of household. He'd have to file as single, which has worse tax rates and a lower standard deduction. That would probably hurt him more financially than whatever benefit OP might share from illegally claiming the kid.

Thanks for explaining that. Makes sense why he'd want someone else to claim his kid if he's not making enough to benefit from the credits, but sounds like he'd lose the head of household status which is pretty valuable.

How do you handle insurance and registration for the 100% business car? Do you put that in your business name? My insurance was weird about covering a personal vehicle used primarily for business.

I have the business vehicle registered and insured under my LLC name with a commercial auto policy. You're right that it can be tricky with personal policies - many won't properly cover business use or will charge extra. The commercial policy actually ended up being around the same price after shopping around, and it provides better coverage for my situation. The registration in the business name also makes it clearer to the IRS that it's a dedicated business asset. One thing to note though - if you go this route, you need to be disciplined about never using that vehicle for personal trips, not even stopping for personal errands during business trips.

Did you have to pay a higher rate for a business lease vs a personal one? I looked into this and the dealer wanted to charge me more when I mentioned it was for my business.

Thank you for this advice! I definitely need to fix this for next year. How do I calculate how much to pay for quarterly estimated taxes? And where exactly on the W4 do I add extra withholding?

For estimated quarterly taxes, you can use the worksheet that comes with Form 1040-ES. Basically, you estimate your total tax liability for the year and divide by four. Pay special attention to your 1099 income - you generally need to set aside about 30-35% of that for taxes (15.3% for self-employment tax plus your income tax rate). For the W4, look at Step 4(c) "Extra withholding." You can put any additional amount you want withheld from each paycheck. If you have multiple W2 jobs, there's also a "Multiple Jobs Worksheet" that can help calculate this more precisely. Your HR department should be able to provide you with a new W4 form to update this information.

I amended last year and it was actually pretty easy. Just file Form 1040-X and include any updated forms that changed. FreeTaxUSA can help you prepare an amended return too. Just be aware that processing times are really slow right now - mine took about 4 months.

Thanks for sharing your experience! That's encouraging to hear it went smoothly for you. Did your attorney try to argue that he was entitled to credit for teaching you the process or anything like that? I'm worried mine might try to claim I'm only able to do it myself because of his "expertise" he shared over the years.

Not at all! The agreement was for his services on a per-appeal basis, not for "teaching" me anything. It's like hiring a plumber - they don't get to claim a percentage of all future savings on your water bill just because you watched them fix your pipes. Property tax appeals are a standard process that anyone can learn. The forms and procedures are publicly available, and what constitutes a valid comparable property isn't some proprietary secret. Your attorney doesn't own the concept of property tax appeals. Just make sure you're not in the middle of an active appeal when you end things. Complete the current cycle, pay what you owe under your agreement, then notify him before the next cycle begins that you'll be handling it yourself going forward.

I used PropertyTaxLowerer.com last year and it was pretty good. Not free but WAY cheaper than giving up 50% to an attorney. They helped identify comps and filled out all the paperwork. I just had to sign and mail it.

This is incorrect information. Property taxes cannot be added to your basis for inherited property. They're either deductible in the year paid (if you itemize) or not deductible at all. Only capital improvements can be added to basis.