This is going to be a weird one. When I was 18, I bought my first house (live in at the time). I moved out about 4 years ago, and had a buddy staying there without paying rent. Agreement was that he payed the utilities and insurance, and as long as he up-kept the property, I wouldn't charge for rent. Within the last week, I finally ended up just selling the house to him for a menial amount (tired of paying the property tax essentially). I would like to investigate if I can perform a 1031 exchange, but since it didn't generate rental revenue, I'm not sure if it would qualify. I have an actual rental house that I'm hoping to close on later this month, so this would be the contender. Any guidance on this, or would it just be better to just pay the taxes? (Sold for $1000, bought for $5000 back 10 years ago, so it'd be a loss).