This is such a great question! I went through the exact same confusion last year. Just to add to what Grant mentioned - make sure you're also considering the timing of your HSA contributions for maximum benefit. If you make HSA contributions through payroll deduction, those reduce your MAGI automatically since they're pre-tax. But if you make direct contributions to your HSA (like if you have a better investment platform with your own HSA provider), you'll need to deduct those on your tax return to get the MAGI reduction. Also, don't forget about the catch-up contribution! If either you or your wife are 55 or older, you can contribute an additional $1,000 to your HSA, which would further reduce your MAGI and help with that Roth IRA phase-out range. One more tip - consider making your HSA contributions early in the year if possible. Unlike IRA contributions which you can make up until the tax filing deadline, HSA contributions for 2025 need to be made by December 31, 2025. Planning ahead will help you optimize both your HSA and Roth IRA strategies!

Great discussion everyone! I wanted to add one more consideration that might help with your planning - the backdoor Roth IRA strategy. Even if your MAGI ends up being too high for direct Roth IRA contributions after accounting for HSA contributions, you can still do a backdoor Roth conversion. This involves contributing to a traditional IRA (which has no income limits) and then converting it to a Roth IRA. The key thing to watch out for is the pro-rata rule if you have existing traditional IRA balances. But if you don't have any traditional IRA assets, the backdoor Roth is a clean way to get that $7,000 per person into Roth accounts regardless of your income level. This might give you more flexibility in your HSA contribution strategy too - you could prioritize maxing out your HSA for the triple tax advantage (deductible, tax-free growth, tax-free withdrawals for medical expenses) and then use the backdoor Roth for your retirement savings goals. Just make sure to keep good records of the conversion for tax purposes!

As a tax professional, I can confirm everything that's been said here is accurate. You absolutely do NOT need to attach 1099 forms that don't show withholding, whether you're e-filing or paper filing. The IRS receives these forms directly from issuers through their Information Returns Processing (IRP) system. One additional tip I'd add: if you're using tax software, double-check that it's pulling the correct amounts from each 1099 into the right schedules. I've seen cases where taxpayers accidentally reported the same income twice (once from manual entry and once from auto-import) or missed reporting certain types of distributions. Also, keep in mind that some 1099-MISC income might require you to pay self-employment tax if it's for services you provided, so make sure you understand what type of income each 1099-MISC represents. The box number on the form will give you a clue about how it should be treated. Your instinct is right - focus on accurate reporting rather than worrying about attachments!

This has been such a helpful thread! I'm in a similar situation with multiple 1099s and was definitely overthinking the attachment requirement. Reading through everyone's experiences and advice has really clarified things for me. Just wanted to add one more tip that helped me stay organized this year - I created a simple spreadsheet early in tax season with columns for each type of 1099 (DIV, INT, MISC, B) and the amounts from each one. Then I have another column noting which schedule or form each amount needs to be reported on. This way I can easily cross-reference while filling out my return and make sure I haven't missed anything or double-counted. It's amazing how much stress gets eliminated once you realize the IRS already has all this information and you just need to report it accurately on the right forms. Thanks to everyone who shared their knowledge here - this community is incredibly valuable for navigating tax season confusion!

Has anyone considered getting the surgery done in another country? I had a full body lift in Mexico for less than half the US price after my 130lb weight loss, and the quality was excellent. Makes the tax deduction less critical when the base cost is so much lower.

I went through this exact situation two years ago after losing 200+ pounds. The key is having rock-solid medical documentation that clearly establishes the procedures as treating medical conditions, not cosmetic enhancement. Make sure your doctors explicitly document the infections, rashes, hygiene issues, and functional problems caused by the excess skin. For the diastasis recti, get documentation of the back pain, posture problems, and incontinence issues. The IRS wants to see that you're treating medical conditions that existed before you decided on surgery. I successfully deducted my panniculectomy and hernia repair as medical expenses. The total was around $19,000, and since it exceeded 7.5% of my AGI, I got a significant deduction. Just be prepared - the IRS may scrutinize these claims more carefully, so having thorough documentation from multiple healthcare providers really helps your case. Also consider timing - if you can bunch other medical expenses into the same tax year (like related medications, follow-up treatments, compression garments), it helps you reach that 7.5% threshold more easily.

Just wanted to add another perspective here - I work as a tax preparer and see this situation a lot with clients. One thing that often gets overlooked is that some states have "safe harbor" rules for part-year residents that can actually work in your favor. Since you sold the stocks while still an Oregon resident, Oregon will definitely tax those gains. But here's something to consider: make sure you're taking advantage of any credits for taxes paid to other states. When you file your Colorado return, you should be able to claim a credit for taxes paid to Oregon on the same income, which prevents true double taxation. Also, document everything about your move timeline. Colorado may want to see proof of when you actually established residency there - utility bills, lease agreements, employment start date, etc. This helps establish the clear cutoff date for which state taxes which income. The $65k gain is substantial enough that it's probably worth consulting with a tax professional who specializes in multi-state returns, especially since Oregon and Colorado have different rules about how they treat capital gains.

This is a really complex situation, and you're smart to be thinking about it now before tax season hits. From what I understand, since you were still an Oregon resident when you sold those stocks, Oregon will likely claim the right to tax the entire $65k in capital gains at their rates. One thing that might help ease your stress - when you file as a part-year resident in both states, each state typically only taxes the income earned while you were actually living there. So Colorado shouldn't double-tax those gains since they were realized before you moved there. The timing is unfortunate from a tax perspective since Oregon treats capital gains as regular income (so potentially higher rates), but what's done is done. For future reference, this is exactly why some people delay major asset sales until after they've established residency in lower-tax states. My advice would be to start gathering all your documentation now: the exact dates of your move, employment start date in Colorado, when you closed on housing, utility transfers, etc. You'll need this to clearly establish your residency timeline for both states. Given the size of those gains, it might be worth consulting with a tax pro who handles multi-state returns - the cost will probably be worth it to make sure you're not leaving money on the table or missing any deductions.

How does everyone track the 74% rental vs 26% personal use split accurately? I'm using a spreadsheet but it's getting super confusing with all the different categories of expenses.

Just went through this exact scenario last year! One thing that really helped me was creating a detailed timeline of when the property transitioned from personal to rental use. I marked the exact date I moved out as my primary residence versus when it became available for rent - these can be different dates and it matters for your calculations. Also, don't forget about the "de minimis safe harbor" rule if you have small repairs during the transition. Items under $2,500 can often be fully deducted in the year incurred rather than depreciated, which can be beneficial for expenses incurred while preparing the property for rental. For your 74%/26% split, make sure you're using the right method - some expenses get allocated based on time (like utilities), while others might need to be allocated based on square footage if you're dealing with mixed-use spaces. The IRS is pretty specific about which allocation method to use for different types of expenses.