Newsflash: X-post from personalfinance about maybe renting my condo to my contractor during repairs.

I’ve got an investment high-rise condo in a major metropolitan city in the US that I’m renting out going on 10 years now. 8 years left on a 30yr mortgage. The unit needs to be updated badly. A realtor said that I can sell right now and do OK with it or get higher rent, more equity, and better returns on a sale by replacing the 30-year old parquet floor and most of the kitchen. The building is also doing renovations like new elevators, a new A/C system, re-lining the pool, etc. The condo was built in the 1960’s and development nearby is expanding. Some of the new condos 3 blocks away are luxe and are renting for 2.5x the rent I can get, so the immediate area is revitalizing. I’ve never had a hard time placing people here at break-even money, but the HOA fees are going up again and we’re about at the point that I will have to pay cash every month to keep renting the place to someone. Sure, there’s equity building, but the HOA fees are well above the mortgage now.The HOA has a cap on how many units can be rented so once the tenant moves out in August, I have only 60 days to do all work and place a new tenant before my spot will be given to someone on the waiting list. That list runs about 4 years long. The management company enforces a 12 month minimum lease.The contractor/personal friend who did storm damage repairs in my own home will be contracted for the work in the condo. In planning it, he just lost his roommate and suggested moving into my condo and doing the work during his lease.Pro: I like his work. I live in it every day. He’s petitioning to get full custody of his child so I trust his need to keep stains off his record. If it goes to heck, we aren’t so close as friends that it would be a terrible loss.Con: You just don’t do this, do you?My thoughts were to stick with arms-length transactions. He pays rent on time as any tenant would, regardless of projects. I pay for parts and labor as the jobs are started and completed and inspect them myself regardless of the lease.What else does this community recommend?Thank you



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