Thanks for this suggestion! I do work full-time though and make about $38k per year, so I don't think I'd qualify as his dependent? We split all expenses pretty evenly.

You're right - with that income level, you definitely wouldn't qualify as a dependent. The income limit for a qualifying relative in 2023 is $4,400, and you're well above that. And since you split expenses evenly rather than him providing more than half your support, that would disqualify you anyway. Thanks for the additional info! It's always good to explore all possibilities, but in this case, it looks like neither of you will get tax benefits from your living arrangement.

This! I work in property management and we definitely notice when someone is living in a unit who's not on the lease. Maintenance visits, neighbors mentioning things, security cameras in common areas, etc. The tax stuff is probably the least of your concerns.

Thanks for the organization tips! Did you include explanations directly on the cover sheet or separate explanation pages for each question? And did you use any particular format that seemed to work well? I want to make this as painless as possible for both me and whoever reviews my case.

I created a master cover sheet listing all questions and what was included for each, then for complex items I added separate explanation pages with more detail. For example, "Question 12: Home Office Deduction - See floor plan on page 5, utility bills on pages 6-8, and explanation of business use on page 9." The format that worked best was using a clear numbering system matching their questions exactly. I used dividers between sections and paper-clipped related documents together. I also highlighted relevant information on bank statements or lengthy documents. The agent who handled my last audit specifically mentioned that my organization made their job easier, which I think contributed to a favorable outcome!

Yes! I appealed an audit decision and won about 70% of what they initially disallowed. The key was providing additional context that showed why those expenses were actually ordinary and necessary in MY specific industry. I included articles about standard practices in my field and letters from colleagues confirming these were normal business expenses for our type of work.

1 That's actually what I'm planning to do come January when I start my new full-time job, but my concern is about the remaining months of this year where I'm only self-employed. Do you know if there's a minimum threshold of income where quarterly payments become required?

22 The general rule is that you need to make estimated tax payments if you expect to owe $1,000 or more in taxes when you file your return. So if your self-employment income between now and December will result in less than $1,000 in additional tax, you might not need to make quarterly payments. Another consideration is that penalties are calculated based on each quarterly period separately. Since you started self-employment recently, you may only need to worry about the remaining quarters of this year rather than all four periods.

4 I used it last year and found it overestimated what I needed to pay each quarter. I think it doesn't factor in all deductions until you complete your final return. I switched to QuickBooks Self-Employed which gives me more real-time estimates based on my actual expenses and income.

16 Wait seriously? I did some small jobs last year for like $200 each and never got 1099s so I didn't report them. Should I be worried?

12 You shouldn't receive a 1099 until after the tax year ends. Companies are required to send them out by January 31st of the following year. So if you did work in 2024, you won't get your 1099 until January 2025. If you did work in the previous tax year and still haven't received a 1099 by mid-February, you should contact your client. Remember though, even without a 1099, you're still required to report all income you earned.

That's terrifying! Did you end up having to pay NY taxes even after moving to Florida? I'm wondering if I should just do this properly from the start and actually spend most of my time in Florida, or if it's not worth the hassle.

I managed to prove I was in Florida for most of the year so I didn't end up owing NY taxes, but it was incredibly stressful and time-consuming. I had to hire a tax attorney which cost about $7,000. The audit lasted over 8 months. If you're serious about changing residency, I'd absolutely recommend doing it properly from the start. The "183 day rule" is just the beginning - you need to genuinely relocate your life. If you're only planning to be in Florida 3-4 months while keeping your Illinois apartment as your main home, you'll almost certainly still be considered an Illinois resident for tax purposes. The penalties for incorrect filing can include back taxes, interest, and significant penalties. Some states can look back several years if they believe you've been improperly claiming non-residency. It's really not worth trying to game the system unless you're actually making a legitimate move.

My company says they can only have me registered in one state at a time for payroll purposes. Would that cause problems if I'm splitting time between two states?

That's a common limitation with many employers, and it can definitely create complications. If your company will only register you in one state for payroll purposes, but you're actually working from multiple states, you may end up with a mismatch between your tax withholdings and your actual tax obligations. If you establish Florida as your legal domicile but still work from Illinois part of the year, you might still owe Illinois taxes on income earned while physically working there, even if no Illinois taxes are being withheld from your paychecks. This would mean you'd need to track your working days in each location very carefully and potentially file part-year or non-resident returns in Illinois, paying additional taxes out of pocket rather than through withholding. This is why many remote workers who split time between states end up committing fully to their no-tax state residence, minimizing time in high-tax states to avoid these complications. The paperwork and compliance requirements can quickly become very complex when you're splitting time.