Yes you would need to report this as rental income. Your insurance should cover but you would really need to know what kind of coverage you have or talk to your agent. Also need to consider if you have coverage or enough coverage if your renter gets hurt or something happens to a guest. I listed my place on craigslist and the first person that looked at it was great and has lived there about three years so no horror stories from me yet. Probably need luck on your side, can't really profile as it may lead to a potential lawsuit against you. Can have general requirements like no pets or smoking but once you start asking about gender, race, marital status, age, children you are opening yourself up to discrimination.