The community wisdom on this is pretty consistent: run the numbers both ways before deciding. Most tax software allows you to calculate both scenarios before finalizing. In my experience, MFJ is better for about 95% of couples, but those 5% where MFS works better usually see SIGNIFICANT benefits that make it worthwhile. What's your specific concern about filing jointly vs separately?

As someone new to this community, I really appreciate all the detailed responses here! I had no idea about the rule that if one spouse itemizes when filing separately, both spouses must itemize - that's a crucial detail that could significantly impact the decision. One thing I'm curious about that hasn't been mentioned yet: how does the timing work if you want to change your mind? Like if you file separately in April but then realize joint would have been better, is there a way to amend and switch filing statuses for that tax year? Or are you locked in once you submit? Also, for anyone who has experience with both methods - how much more complicated is the paperwork when filing separately? Does it essentially double the work since you're preparing two returns instead of one?

I think everyone is overlooking an important aspect of multi-state partnership reporting - the withholding requirements. Many states require partnerships to withhold taxes for nonresident partners, regardless of whether you ultimately need to file a return there. Check your K-1s carefully - they should indicate if any state taxes were withheld on your behalf. If taxes were withheld, you'll likely need to file a nonresident return in that state, even if you otherwise wouldn't have a filing requirement, just to get a refund of over-withheld amounts. This happened to me with a partnership that withheld Oregon state taxes at their highest marginal rate, but after applying deductions and credits, my actual Oregon liability was much lower. I had to file an Oregon nonresident return to get back about $2,300 in over-withheld taxes.

This is a really comprehensive discussion! I wanted to add one more consideration that might apply to your situation - apportionment factors for multi-state partnerships. Since your Colorado partnership is investing in real estate across multiple states, you'll want to understand how each state apportions partnership income. Some states use a single sales factor, others use three-factor formulas (property, payroll, sales), and this can affect how much of the partnership's income is actually subject to tax in each state. For real estate partnerships specifically, most states will source the income to where the property is physically located. But if the Colorado partnership is also engaged in management activities (property management, development decisions, etc.), some of that income might be sourced to Colorado based on where those business activities occur. I'd recommend asking your partnership for a breakdown of how they've allocated income by state on their partnership returns. This information should help you understand not just which states might require filings, but also how much income is actually attributable to each state. Sometimes the state-by-state breakdown is much different than what you might assume just from looking at where the underlying properties are located.

Not directly related to your immediate question but since you're just starting a new job after a gap: remember that your 2024 withholding might seem wrong all year because the system assumes you've been making that $22/hour since January. If you've been unemployed most of the year, you might end up having too MUCH withheld relative to what you'll actually owe. Just something to keep in mind when you're looking at your paychecks after fixing the current $0 withholding issue.

This is a really common issue with the redesigned W4! The good news is that it's likely fixable. Since you only filled out steps 1 and 5, the payroll system is making assumptions about your tax situation that might not be accurate for your specific pay schedule and start date. Here's what I'd recommend: Wait for your next full two-week paycheck to see if withholding appears once the system has better data about your actual earning pattern. If there's still no FITW on that check, you'll need to submit a new W4 with an additional withholding amount in Step 4(c). A quick calculation: At $22/hour for 40 hours/week, you're looking at about $45,760 annually. Even with the standard deduction, you'd owe roughly $3,900-4,200 in federal taxes for the year. If you end up needing to add extra withholding, putting around $80-85 per paycheck in Step 4(c) should get you close to the right amount. Don't panic though - catching this early means you have plenty of time to correct it before tax season!

Hey Zara! I went through something very similar with my disability discrimination settlement last year. You're right to be confused - the lack of tax forms doesn't mean you're off the hook for reporting it. Based on my experience and what my tax attorney told me, you'll need to report the full gross settlement amount ($20,250) as "Other Income" on your Form 1040. The good news is that you can deduct the attorney fees ($6,750) as an adjustment to income on Schedule 1, Line 24 under "Attorney fees and court costs for unlawful discrimination claims." The key thing is that employment discrimination settlements like yours still qualify for the attorney fee deduction even after the Tax Cuts and Jobs Act - this is specifically preserved under IRC Section 62(a)(20). I'd strongly recommend keeping detailed records of everything: the settlement agreement, any correspondence with your attorney about the fee arrangement, and documentation showing this was specifically for disability discrimination. The IRS may not have forms from your employer, but they could still ask questions later. One more tip - if any portion of your settlement was specifically allocated to physical injury or sickness caused by the discrimination (like medical expenses for stress-related symptoms), that portion might be excludable from income under Section 104(a)(2). Check your settlement agreement to see if there's any such allocation. Good luck with your return!

I've been following this thread with interest since I'm dealing with a similar situation. One thing I haven't seen mentioned yet is the timing aspect - Zara, when did you actually receive the settlement funds? The tax year for reporting is typically when you received the money, not when the case was resolved or the agreement was signed. Also, I'd recommend being very specific about the description when you report it as "Other Income." Something like "Employment Disability Discrimination Settlement" will be clearer for the IRS than just a generic description. This helps establish the nature of the income and supports your ability to deduct the attorney fees under Section 62(a)(20). One more consideration - if your settlement included any punitive damages, those are generally fully taxable regardless of the underlying discrimination claim. The settlement agreement should specify if any portion was punitive damages versus compensatory damages. The distinction can affect how different portions are taxed. Keep all your documentation organized and consider making copies for your records. Even though you didn't receive a 1099, having a clear paper trail will be invaluable if there are ever any questions about how you reported this income.

Has anyone considered that it might just be easier to get a prenup? I'm not a lawyer but wouldn't that be a simpler way to establish which assets are pre-marital vs. marital property, including the entire HSA account?

I'm a tax attorney who's dealt with this exact scenario multiple times. The consensus here is correct - you absolutely cannot open a new HSA without current HDHP coverage, even for transfers from existing HSAs. However, I want to address the underlying asset protection concern. While detailed record-keeping is helpful, it's not bulletproof in divorce proceedings. Courts can still rule that investment growth during marriage constitutes marital property regardless of your documentation. The prenup suggestion is spot-on and would be much more legally robust. You could specify that your entire HSA (including future appreciation) remains separate property. Alternatively, the prenup could establish that only the pre-marital balance stays separate, with post-marriage growth being marital property - which achieves exactly what you were trying to do with separate accounts. Given that you're getting married in a few months, consulting with a family law attorney about including HSA provisions in a prenup would be far more effective than trying to navigate HSA eligibility rules. The legal protection would be stronger and you wouldn't have to wait for open enrollment periods or manage multiple accounts.