Has anyone used TurboTax to report this kind of situation? Does it have a good section for handling insurance payments on rental properties or should I use a different tax software?

I dealt with this exact situation last year when my rental unit had flood damage. The key thing to understand is that you need to separate the personal use portion from the rental portion of your property for tax purposes. For the rental portion: If you received $7,800 but only spent $4,600 on actual repairs (the $7,800 minus the $3,200 you used elsewhere), then that $3,200 difference is generally taxable income that should be reported on Schedule E. This is because you essentially converted insurance proceeds into cash for other purposes. For documentation, keep all your receipts for materials you bought for the DIY repairs. The IRS doesn't allow you to count your own labor, but material costs definitely count toward legitimate repair expenses. The insurance company will likely send you a 1099-MISC if the payout was over $600, but that doesn't mean the entire amount is taxable - just that they reported the payment to the IRS. My advice: Calculate what percentage of your property is used for rental, apply that percentage to both the insurance payout and your actual repair costs, then report any excess on Schedule E. Better to be conservative and report it than get caught in an audit later!

Anyone know if Vanguard generally fixes these 1099-R issues quickly? I have a similar problem but with Fidelity and I'm getting anxious about tax deadlines approaching.

This is a really common misunderstanding with brokerages! You're absolutely correct based on the IRS rules. I work in tax compliance and see this issue frequently - the key is that recharacterizations are tied to the tax year of the original contribution, not when the transfer physically settles. Since both of your recharacterizations were for 2023 contributions and both were completed before your 2023 tax filing deadline, they should both be reported for tax year 2023. The fact that one settled in January 2024 is irrelevant. When you call Vanguard back, specifically ask for their "Retirement Services Tax Team" or "IRA Tax Specialist" rather than general customer service. Have Publication 590-A ready with the exact quotes you mentioned. Most importantly, reference the "timing" rule you cited - it's very clear that the election and transfer must both occur before the filing deadline for the contribution year. If they still push back, ask them to cite which specific IRS publication supports their position. They won't be able to because the rules are clear. Document everything in case you need to escalate to a supervisor.

Has anyone considered using the new 1023-EZ form? It's way shorter than the regular application and only costs $275 instead of $600.

Just went through this exact process with our university's robotics club last year! A few practical tips that might help: 1. **Start with your student activities office** - They often have templates and can fast-track the state incorporation process. Ours had a relationship with the Secretary of State's office that cut our waiting time in half. 2. **Consider the "substantially all" test carefully** - For 501(c)(7) social clubs, the IRS requires that substantially all (generally 85%+) of your activities be for members' pleasure/recreation. If you're doing educational outreach or community tournaments, that might push you toward 501(c)(3) instead. 3. **Document everything now** - Start keeping detailed records of your current activities, membership, and any income/expenses. The IRS will want to see your operational history. 4. **Talk to your sponsor about timing** - Many sponsors are willing to work with "application pending" status, especially if you can show them your filed paperwork. This gives you breathing room on the 3-month timeline. The whole process took us about 4 months total, but having that sponsor conversation early really helped manage expectations. Good luck with your application!

Has anyone tried the TurboTax Self-Employed app? My accountant charges me $650 to file my taxes each year and I'm wondering if I could just do it myself with good software. I've got about 20 clients and mostly standard expenses like software, computer equipment, and my home office.

I've been using a combination approach that's worked really well for my freelance photography business. For day-to-day expense tracking, I use Mint (which is free) connected to my business checking account and credit card. It automatically categorizes most transactions and I just review them weekly to make sure everything's labeled correctly. For invoicing and more detailed business tracking, I use FreshBooks. The mobile app is great for capturing receipts on the go, and it integrates well with my bank accounts. The real game-changer though has been setting up automatic transfers. I put 30% of every client payment into a separate "tax savings" account immediately. No more scrambling to find money for quarterly payments! One thing I learned the hard way - whatever system you choose, start using it consistently from day one. I tried to go back and categorize a whole year's worth of transactions once and it was absolutely brutal. Better to spend 10 minutes a week staying on top of it than 3 weekends at the end of the year trying to catch up.

One thing nobody's mentioned yet - if you're using tax software, be super careful with how you enter home improvements. I accidentally entered my bathroom remodel as a "home office improvement" in TurboTax last year, and ended up with an inflated deduction. Found the mistake during a review and had to fix it, but it was easy to mess up! For the cost basis question - yes, kitchen renovations increase your overall home's cost basis, but they're tracked separately from your business deductions. Keep excellent records of all home improvements regardless of whether they qualify for immediate business deductions. You'll need them when you sell.

Slightly off topic but if u have other big expenses coming up that would affect your office directly, maybe consider waiting til next year to switch to the simplified method. I had a similar situation where I was doing actual expenses for years, then did a renovation that had nothin to do with my office. Kept actual expenses that year, then the next year I needed new windows (including in my office) and a roof repair, so I stayed with actual expenses for one more year. THEN I switched to simplified the year after when I had no major house expenses. Timing things can make a difference!