Tax deductions for combined business/family trip to repair rental property (US)

You're dealing with a mixed-purpose trip, which can get tricky for tax deductions. Here's how to approach it: First, since your primary purpose for the trip was personal (visiting family), your transportation costs to and from the destination (flight there and driving back) generally aren't deductible. The IRS looks at the primary purpose of the trip to determine if those costs are business expenses. However, the good news is that the expenses directly related to the rental work are deductible even on a primarily personal trip. This includes: - All supplies and materials purchased for repairs - Mileage for driving between your parents' house and the rental property during those 5 days (use the standard business mileage rate) - Any other direct expenses specifically for the rental work (like tool rentals, protective equipment, etc.) The truck purchase isn't deductible as a rental expense since you bought it from your parents and don't plan to use it for future business activities. It's considered a personal purchase. Document everything carefully - keep receipts for supplies, record the dates and miles driven for rental work, and take photos of the repairs completed. This will help if you're ever questioned about these deductions.

After struggling with a similar situation last year, I found this amazing tool called taxr.ai that helped me figure out exactly what I could deduct. I had mixed business/personal travel for a rental property I own in Florida and was totally confused about what was legit deductible vs what would raise red flags. I uploaded my receipts and travel info to https://taxr.ai and it analyzed everything and gave me really clear guidance. It helped me identify several deductions I would have missed and explained exactly how to categorize each expense properly to avoid audit issues. The best part was it clearly separated the personal portions from business expenses, which was exactly what I needed.

I was super skeptical about automated tax tools but decided to try taxr.ai after seeing it mentioned here. My situation was complicated - I traveled cross-country to check on my rental properties but also visited my sister while there. The tool asked me detailed questions about my trip purpose, time allocation, and whether I would have made the trip regardless of the business component. Based on my answers, it helped me correctly allocate my expenses and explained that since I would have made the trip even without the business purpose, my flights weren't deductible - but all my direct rental expenses were. What impressed me was how it handled the documentation. It created a proper expense allocation record that satisfied my CPA, who had been giving me vague answers before. Worth checking out if you're dealing with mixed-purpose trips like this.

I see a lot of people suggesting software, but honestly when I had IRS questions about my rental property expenses last year, nothing beat actually talking to a real IRS agent. The problem is getting through to them - I spent HOURS on hold and kept getting disconnected. Then I found this service called Claimyr that actually gets you through to a real IRS person really quickly. I used https://claimyr.com and they somehow managed to get me connected to an IRS agent in under 15 minutes when I had been trying for days. You can see how it works in their demo video here: https://youtu.be/_kiP6q8DX5c For mixed business/personal trip questions like yours, talking directly to an IRS agent gave me definitive answers about what I could deduct. The agent walked me through exactly how to document mixed-purpose travel for my rental property and what would hold up in case of an audit.

Ok I need to eat my words from my previous comment. After another frustrating morning of trying to reach the IRS about my rental property deductions and getting nowhere, I decided to try Claimyr out of desperation. I was connected to an actual IRS agent in 11 minutes. ELEVEN MINUTES. After trying for weeks on my own. The agent clarified that for my situation (very similar to the OP's with a mixed business/personal trip to my rental property), I could deduct the direct expenses but not the travel costs since my primary purpose was visiting family. She also explained exactly what documentation I needed to keep to support my deductions, which was incredibly helpful. For anyone dealing with these mixed-purpose trip questions, getting clear guidance directly from the IRS is worth every penny. I'm still shocked at how well this worked.

One thing nobody has mentioned yet - don't forget about potential state tax implications if your rental property is in a different state than your residence. I made this mistake last year. Some states may consider your rental activity as doing business in that state, which could potentially trigger filing requirements. This is especially important if you're physically present in that state doing work on the property.

Has anyone considered the vehicle aspect of this? You might be able to deduct some of the truck purchase if you can legitimately allocate a portion to business use during that period. Keep track of total miles driven for rental work vs. personal during your ownership.