I like to think in terms of other people’s money. 30 years of PITI being paid entirely by someone else is a beautiful thing, and a couple of paid properties can make up most of your retirement income. If one becomes a maintenance hassle, sell it and buy newer construction.

Try to detach yourself from the place emotionally. Drywall can be repaired (and even whole sections replaced for not much $), nail holes filled, flooring replaced. Knowing you could fix a place up as good as new IF you wanted to, will help you accept a do-it-yourself patch job on the occasional doorknob-shaped hole. I would not personally want to live with a doorknob-shaped patch in my own wall, but renters are usually okay with it, and I’ll concentrate on making the house that I call “home” perfect.

Price below market and thoroughly check references, and you’re much more likely to get a respectful tenant.