Do mortgage points get deducted all at once in the year you buy, or do they have to be spread out over the life of the loan? I've heard conflicting info.

Points can be tricky. For your main home, if the points meet certain IRS criteria, you can deduct them fully in the year you paid them. Otherwise, you have to spread the deduction over the life of the loan. To deduct them all at once, the points need to be for your primary residence, be a standard practice in your area, not be excessive, and a few other requirements. If it's a refinance rather than a purchase, you typically have to amortize the points over the loan term.

I always get confused about whether I should itemize or take the standard deduction. Is there an easy way to know which is better without doing all the work to itemize first?

Oh that's really helpful! My dad sold his house about 3 years ago and has been renting since then, so it sounds like he would qualify. Does the money have to go directly to the home purchase, or can he just give it to me and then I use it for the down payment?

Sounds like your dad would qualify since he's been renting for the past 3 years. That meets the IRS definition of a first-time homebuyer. Regarding the funds, your father should take the distribution directly from his IRA and then use those funds toward your home purchase. While there's no specific requirement that the money has to go directly from the IRA to the title company, the IRS does look at the purpose of the withdrawal. The safest approach would be for him to document that he's using the funds for your qualifying first-time home purchase. Have him keep records showing the withdrawal and then either a gift letter to you or direct payment toward closing costs or down payment.

I used mine 3 years ago without issues. Just make sure you keep all documentation: IRA withdrawal statements, closing documents, proof the funds were used for the home purchase within 120 days, etc. As long as you're following the rules and have documentation, you should be fine even if audited.

I had no idea about penalty abatement! Would that work even though it's been so long since the original due date? And do I need to have the return filed first before I can request this?

Yes, you can still request penalty abatement even after a significant delay. The IRS doesn't have a strict deadline for requesting abatement, though they're generally more receptive when you're actively trying to resolve the situation by filing your return and making payment arrangements. You absolutely need to file the return first before requesting any kind of penalty abatement. The IRS won't consider penalty relief on unfiled returns. Once your return is filed, you can request First-Time Penalty Abatement if you had a clean compliance history for the three years prior to 2021. If you had legitimate reasons for not filing (serious illness, natural disaster, etc.), you could alternatively request Reasonable Cause abatement with supporting documentation.

Those calculations seem high. Doesn't the failure-to-pay penalty cap at 25% just like the failure-to-file penalty? I thought the combined penalties couldn't exceed 47.5% of the original tax.

Thanks, that's really helpful about the lump sum election. I hadn't even thought about the tax implications of getting disability backpay. Do you know if I would need to file amended returns for the previous years in that case, or is it handled differently?

You don't need to file amended returns for the previous years with a lump sum election. Instead, when you file your taxes for the year you receive the backpay, there's a special calculation that's done on that year's return. The SSA will send you a letter (SSA-1099) showing how much of your payment applies to each previous year. Your tax preparer (or tax software) can then use this information to calculate your tax as if the income had been received in those earlier years, potentially putting you in a lower tax bracket for the lump sum. It's a bit complex, but any tax professional familiar with disability claims should know how to handle it. And definitely keep all documentation about your medical expenses, as some of those might be deductible as well.

I second the VITA suggestion. I used them when I was in college and they were great. Just make sure to bring all your documentation - they'll want to see your ID and social security card, plus any income info you have (even if it's just printouts from the survey sites showing your earnings).

Does having utilities in your name at the Florida address help? My parents let me keep the internet bill in my name and I pay it monthly even while I'm away on assignments. Is that enough of a substantial expense?

A utility bill in your name is helpful as supporting documentation, but probably not sufficient on its own as your only "substantial" expense. The IRS is looking for significant financial burden - essentially costs that would motivate you to return to that location to make the expense worthwhile. Internet bills are typically under $100/month, which might not be considered substantial enough. Combine it with other regular expenses like a formal rental agreement, storage unit costs, car payments/insurance for a vehicle kept at that location, etc. The key is showing you're maintaining a financial life in Florida even when you're not physically there. Multiple smaller expenses can add up to demonstrate your commitment to that tax home.

New York considers you a statutory resident if you maintain a "permanent place of abode" in NY and spend more than 183 days there. Since you're renting a room in NYC and working consistently in the area, you need to be extremely careful with your day count. I'd recommend consulting with a tax professional who specializes in multi-state taxation specifically for healthcare travelers. New York is notoriously aggressive with residency audits, especially with high-income professionals like travel nurses who claim residency in no-income-tax states like Florida.