Just a heads up - if your insurance reimbursed you for any of the damage, you need to subtract that from your casualty loss calculation. The IRS only allows you to deduct losses that weren't covered by insurance. Same goes for any FEMA assistance you received for repairs.

I went through something very similar after Hurricane damage last year. For documentation, I found that taking detailed photos before any cleanup was crucial - I wish I had taken more! The IRS accepts multiple types of evidence for fair market value: 1) Contractor estimates (like others mentioned) - get at least 2-3 if possible 2) Insurance adjuster reports - even if they denied coverage, their damage assessment is valuable 3) Real estate appraisals if you have recent ones 4) Receipts for original purchases when available 5) Online research for replacement costs (save screenshots with dates) For your specific situation with back-to-back storms, make sure to clearly separate the damage from each event since they're different FEMA declarations. I had to create a detailed timeline showing what was damaged in storm #1 vs. what additional damage occurred in storm #2. One thing that caught me off guard - if you're planning to rebuild/repair, keep ALL receipts. Sometimes the actual repair costs can help support your "difference in value" calculations, especially if contractors find additional damage during the work that wasn't initially visible. The key is having a paper trail for everything. The IRS wants to see that you made reasonable efforts to establish fair values, not necessarily that you hired expensive appraisers.

quick question - wouldn't this situation be simpler if the parents just reported the entire sale on their return since they got most of the money? seems like unnecessary complication for the kid to report anything if they just got a small gift from the proceeds.

@Haley Bennett - I went through something very similar when my mom added me to her house deed before selling. Since your parents gifted you the ownership interest, you definitely need to report your portion even though you only received $6,800. Here's what worked for me: First, figure out your exact ownership percentage from the deed (sounds like it might be equal thirds if all three names are listed). Then on Form 8949, report only your percentage of the $240k proceeds. For basis, since it was a gift from your parents, you'll use your share of their original purchase price plus any improvements they made before gifting your interest. In FreeTaxUSA, when you get to the 1099-S section, there should be an option to edit or override the amounts. Enter your calculated portion and add a description like "Reporting 33.33% ownership interest per deed" in the description field. The key is making sure your reported numbers match your actual ownership percentage, not the cash you received. Don't stress too much - this is actually a common situation and the IRS sees it all the time with family property sales!

Hey OP, just curious - how long have you been trying to get this sorted? I'm in a similar boat and wondering how long I'm gonna be treading water 🏊‍♂️

Based on my experience, here's what I'd recommend for getting that Letter of Indemnity: 1. **Call early in the morning** (like 7-8 AM) - wait times are usually shorter 2. **Have your EIN/SSN ready** plus the exact bank routing/account info 3. **Be super specific** about what the letter needs to say - the IRS reps aren't mind readers 4. **Get a case number** for your request so you can reference it in follow-ups Also, some banks have specific forms they want the IRS to use, so check with your bank first about their requirements. Saved me a lot of back-and-forth when I had to do this for a business account issue. The whole process took about 2-3 weeks for me, but that was with one revision needed. Good luck! 🤞

Question - I'm planning to hold my property for only 5-7 years. Does a cost segregation study still make sense in that case? I've heard there can be depreciation recapture issues when you sell.

I've been through this process twice now with different commercial properties, and I want to echo what others have said about not doing it yourself. The IRS Audit Techniques Guide for Cost Segregation is incredibly detailed and technical - it's not just about identifying components, but properly valuing and documenting them according to specific engineering principles. One thing I learned the hard way on my first property: make sure whoever you hire has experience with your specific property type. Industrial buildings have different segregation opportunities than office buildings or retail spaces. The cost segregation specialist should be familiar with the construction methods and systems typical to your property type. Also, don't forget about the "lookback" provision if you've owned the property for a while. You can still do a cost segregation study on properties you've owned for years and capture missed depreciation through a Form 3115 (Application for Change in Accounting Method). This can result in a significant one-time deduction in the year you file the study. The upfront cost stings, but the cash flow benefits are real. On my 1.2M industrial property, the study cost $12k but generated about $180k in additional depreciation deductions over 7 years.

Don't forget you'll need to track personal vs business mileage separately! The IRS is really picky about this. If you use the same vehicle for both, make sure your Excel sheet clearly distinguishes which trips are for business. Learned this the hard way when I got audited last year over my mileage deductions for my courier service.

This is really helpful info! I'm in a similar situation with consistent routes. One thing I'd add - if you're using Excel, consider adding a column for your vehicle's odometer reading at the start and end of each business day. Even though it's not strictly required by the IRS, it creates a paper trail that shows your total business vs personal mileage split, which can be super valuable if you ever get audited. I learned this from my accountant after she saw how many business miles I was claiming compared to my total annual mileage. Having those odometer readings makes it crystal clear that your business use percentage is legitimate.