Renting my residence

[Diana Meek]

I've been considering real estate investing for a while, but just got a big push. I am having another child and need a less complicated place to live. As it is, I have an acre of land and a house I've been slowly remodeling for a few years, so I'm looking to make a few updates and rent it out with the possibility of coming back to it in a few years when my kids are older and we have fewer commitments outside of our family (grad school, work, etc). A carpenter that I've worked with for years has inquired about renting the house, but the increase in rent from his current place is pretty substantial. I have a relationship with him, so I feel comfortable renting it without a property manager. My husband and I have considered letting him rent it for PITI or a hundred or so less than PITI for the first year if he'll commit to making improvements to the property. The benefit: we have a steady renter who we trust (note, I still have to check his rental history. This assessment could change depending on what I find), and we get great quality upgrades to the property. The cons: without the discount, the house is little out of his price range, and we could get into sticky territory because we'd like to maintain a positive relationship with him. We haven't initiated anything here, just thinking things out. What do you guys think? Bad idea?