Thanks so much for sharing your experience! That's really helpful. Did you guys use any specific software to compare both options? I'm worried about making a mistake if I try to calculate everything manually.

We used TurboTax and just ran through the process twice - once for joint and once for separate. It was tedious but worth it. I'd definitely recommend using some kind of tax software that lets you save different scenarios. The student loan part was trickier - had to use the loan servicer's calculator separately to figure out how much payments would change under each filing status.

This is such an important point! We got hit with this last year and had to file an amendment. Cost us extra in prep fees and delayed our refund by months.

Yep, it's one of those weird tax rules that nobody tells you about until you make the mistake! The other thing that surprised us was that if you file separately, you often can't contribute to a Roth IRA if your income is over a certain threshold, which is much lower for separate filers than joint.

I second this! My closing agent was super helpful when I had a similar question. Sometimes the simplest solution is best.

I didn't even think of that! I just emailed my agent and she got back to me right away. You're right - she had everything on file and sent me the state withholding form with the ID number clearly printed at the top. I was definitely overthinking this whole thing. Thanks for suggesting the obvious solution that I completely missed! Just finished my taxes and everything went through perfectly.

I had the opposite problem! TurboTax kept rejecting my entry when I included the dashes, but accepted it when I removed them. Seems like it might vary by state.

That's so strange! Must definitely depend on the state then. I'm in Illinois - where are you located? Maybe we should specify which states have which requirements when sharing advice like this. I guess the safest approach is to try both with and without special characters if the first attempt gets rejected. TurboTax isn't always clear about the exact format they want for these state-specific entries.

Can you explain more about how this might affect Social Security? I'm planning to sell a rental property next year and I'm already receiving Social Security benefits.

For Social Security, if your combined income (your adjusted gross income + nontaxable interest + half of your Social Security benefits) exceeds certain thresholds, more of your Social Security benefits become taxable. For 2025, if you're filing single and this combined income exceeds $25,000, up to 50% of your benefits may be taxable. Above $34,000, up to 85% can be taxable. For married filing jointly, those thresholds are $32,000 and $44,000 respectively. So a large capital gain could definitely push you over these thresholds, causing more of your Social Security to be taxed.

The tax rate would be the same whether you sell one property or multiple properties in the same year. However, selling multiple properties might give you more flexibility with timing - you could spread the sales across different tax years to potentially keep yourself in a lower capital gains bracket each year.

Do you need an appointment for VITA or can you just walk in? And how long does it usually take?

Most VITA sites require appointments, especially this late in the tax season, but some do accept walk-ins. I'd strongly recommend calling ahead to schedule and ask what documents you need to bring. As for time, it typically takes about 45-60 minutes for a return with a retirement savings credit. That's much faster than learning to do it yourself, especially the first time. The biggest advantage is having someone who knows exactly what they're doing handle your specific situation - they can spot potential issues and maximize your refund while ensuring everything is done correctly.

I tried cash app taxes but they don't support multiple states if you moved during the year. Just a heads up for anyone in that situation.

My LLC is registered in Delaware. I think that's why the company I worked with only mentioned federal forms... Do you know if Delaware has any special requirements for foreign-owned LLCs with no physical presence in the state?

Delaware is actually one of the better states for your situation. They don't require a separate state income tax return for LLCs that don't have physical operations in Delaware. You'll still need to pay the annual Delaware franchise tax ($300 for most small LLCs) to maintain your business registration, but that's separate from income tax filing. Just make sure you've paid that annual franchise tax - Delaware will revoke your LLC status if you miss payments. They send the notice to your registered agent, so sometimes foreign owners miss these notifications if they're not in regular contact with their agent.

This is super important. My friend got hit with a $10,000 penalty for not filing FBAR even though he didn't owe any taxes. The IRS and Treasury Department don't mess around with foreign account reporting.