2 Does anyone know if you need to submit proof of expenses to your HSA administrator when you reimburse yourself? My HSA is through HealthEquity and their website just lets me request distributions without uploading any documentation.

Great question! You're absolutely on the right track with your HSA strategy. Since you established your HSA on October 15th, any qualified medical expenses from that date forward are eligible for reimbursement - which means your November procedure definitely qualifies. You can contribute up to the 2025 maximum ($4,300 for individual coverage, or $8,550 for family coverage if you're 55+) regardless of when during the year you opened the account, thanks to the "last-month rule." Just make sure you maintain your high-deductible health plan through December 2026 to avoid any penalties. Your reimbursement strategy is spot-on too. You can reimburse yourself the current $1,300 now and the remaining $3,000 later as you build up the account. There's no deadline for HSA reimbursements as long as the expense occurred after your HSA was established. Just keep detailed records of all receipts and documentation - the IRS doesn't require you to submit these with your taxes, but you'll need them if audited. One pro tip: if you can afford to leave some money in the HSA to grow, consider only reimbursing what you absolutely need now. HSAs can be great long-term investment vehicles since the money grows tax-free and withdrawals for qualified expenses are always tax-free, even decades later!

I see a lot of advice here but I'm confused about one thing... if I have $5000 in winnings (including a $3000 jackpot) but $7000 in losses for the year, do I still have to report the $5000 as income and then separately deduct $5000 in losses? Or can I just report the net loss of $2000? Does turbo tax handle this correctly?

Something to keep in mind - even if you get your withholding back, you'll need to be prepared for potential scrutiny from the IRS if your gambling losses are substantial compared to your income. They sometimes flag returns where gambling losses seem unusually high relative to someone's financial situation. The key is having rock-solid documentation. Beyond what others have mentioned, I'd also recommend keeping photos of your losing tickets if possible, and if you play table games, try to get pit boss signatures on your session records when you have big losses. Some casinos will do this if you ask. One more tip: if you're planning to claim gambling losses this year, consider opening a separate bank account just for gambling funds next year. It makes tracking much cleaner and provides a clear paper trail of your gambling activity that's separate from your regular expenses.

Great discussion everyone! I just wanted to add one more practical consideration for your situation. Since you're planning to rebalance between your IRA and taxable account, this might be a good time to think about tax-location strategy going forward. Generally, it's most tax-efficient to hold your most tax-inefficient investments (like REITs, bonds, or high-turnover funds) in tax-advantaged accounts like your IRA, while keeping tax-efficient investments (like broad market index funds or individual stocks you plan to hold long-term) in your taxable account where you can benefit from long-term capital gains rates. With 30-40 years until retirement, you've got plenty of time to recover from those tech losses. The silver lining is that this gives you a chance to restructure your portfolio with better tax efficiency in mind. And as others have confirmed, you don't need to worry about wash sale rules when moving from IRA losses to taxable purchases - just focus on building a solid long-term allocation that you can stick with through future market volatility.

One additional thing to consider as you're restructuring - since you mentioned you're 30-40 years from retirement, this might actually be a blessing in disguise. Those tech losses in your IRA, while painful now, don't have the same tax implications as losses in a taxable account would. I went through something similar in 2022 with my growth-heavy IRA getting crushed. What I learned is that IRA losses, while they hurt psychologically, are actually "cleaner" from a tax perspective since you're not missing out on tax-loss harvesting opportunities like you would in a taxable account. The fact that you're thinking about wash sale rules shows you're being thoughtful about this, but as others have confirmed, selling those losing positions in your IRA and buying different investments in your taxable account won't create any wash sale issues. Focus on building a more diversified allocation across your accounts rather than trying to recover those specific losses. With decades until retirement, time is really on your side here. Those ARKK losses might sting now, but they'll be a footnote in your investment journey if you stay disciplined with a solid long-term strategy.

I went through this exact situation last year when I loaned my brother money for his business. One thing I learned that might help others is to set up a simple amortization schedule at the beginning - it makes tracking so much easier throughout the year. You can create one in Excel or Google Sheets that shows each payment broken down into principal and interest portions. This way, you know exactly how much taxable interest income you'll receive each month, and your sister will know exactly how much she owes. Also, make sure to discuss with your sister upfront how she'll handle the interest payments from her tax perspective. She won't be able to deduct the interest since it's personal (not business or mortgage interest), but it's good for both of you to understand the full tax picture before moving forward. The promissory note is definitely essential - I used a simple template I found online that included all the key elements mentioned by others here. Having that formal document made me feel much more confident about the whole arrangement.

Great question! I went through this exact same process when I loaned money to my daughter for her wedding expenses. You're absolutely right that the interest you receive will be taxable income that needs to be reported on your tax return. From my experience, here are the key steps I recommend: 1. **Create a formal promissory note** - This is crucial for IRS documentation. Include the loan amount, interest rate, payment schedule, and what happens if payments are missed. Both parties should sign and date it. 2. **Track payments meticulously** - Keep detailed records separating principal repayment (not taxable) from interest payments (taxable income). I used a simple spreadsheet to track each monthly payment. 3. **Report on Schedule B** - You'll report the interest income on Schedule B of your Form 1040, even without receiving a 1099-INT. Just list your sister's name as the payer and enter the total interest received during the tax year. 4. **Check the Applicable Federal Rate (AFR)** - Since your loan is over $10,000, make sure your 5% interest rate meets or exceeds the current AFR to avoid potential gift tax complications. The IRS publishes these rates monthly. One additional tip: Consider discussing the tax implications with your sister upfront. While she won't be able to deduct the interest payments (since it's personal debt), it's good for both of you to understand the complete picture before moving forward. Having proper documentation from the start will make tax time much smoother and protect both of you if the IRS ever has questions about the arrangement.

Has anyone used a Delaware Statutory Trust (DST) for this kind of situation? I've heard it can work with a 1031 exchange but not sure if it applies when the original property is already in a family trust.

Another strategy worth considering is a Charitable Remainder Trust (CRT) if you have any philanthropic interests. This can be particularly effective for highly appreciated farmland since you get an immediate charitable deduction, avoid capital gains tax on the sale, and receive income for life. The CRT sells the property tax-free, then pays you a percentage annually (typically 5-8%) for either a term of years or your lifetime. At the end, the remainder goes to charity. If you don't need the full value immediately and want to support causes you care about, this could provide steady income while significantly reducing your current tax burden. You could also combine this with life insurance to replace the charitable remainder for your heirs if that's a concern. The tax savings from the charitable deduction can help fund the premium payments.