I've seen personally reasons why I wouldn't put an aircraft I owned on any leaseback with a flight school. In the late 90s after I got my private I continued to rent from the flight school I trained with, one of the aircraft available belonged to Lorenzo Lamas, a very nice guy by the way, it was a brand new PA-28 with leather and A/C. Some of the other renters just didn't seem to respect it and while it didn't fall into disrepair it wasn't taken care of like it would've been had he not put it out for rental. Another example, a friend of mine bought a relatively low time C-150 to commute with, being an A/P also he basically restored it, including new windows, some new avionics, new interior and a new paint job including wheel pants. It turned out very nice. Then he finished his RV-8 and sold it to a friend of his that wanted to teach in it, last I heard the wheel pants aren't on and starting to look a little shabby, sad. As far as buying something that you might want to charter I've seen people spend millions on upgrading interiors and paint and having customers basically disrespect the airplane in ways that are almost inexplicable. If I ever buy an airplane I'd never try to offset the cost by renting it out, I also wouldn't buy an airplane I couldn't afford comfortably without doing so.