Buying a plane....
My buddy had a C-172 that he leased back and was using it to build time in. He as well, put very little money into it and it was paying for itself. He also, got a couple of traffic contracts that he used it for and they paid pretty well. So I started looking. I found mine and it was in great shape (Avionics needed updating). It listed for $38K, booked at about $38.7K, and I offerd $34K. We settled for $35K.
I found a Hurricane Damaged (very little damage) same year C-172 with a fresh engine and a IFR Certified GPS. I bid on it at a auction and picked it up for spare parts (engine, instruments, etc.) and I am selling it off part by part.
Bottom line, the airplane breaks even and I fly it (build time) for free. I just finished my Instrument and I am working on my Commercial. My buddy is selling his ( he is FO on a RJ) as he doesn't fly it anymore. We are considering picking up a cheap twin (C-310) so I can build multi time in and maybe we can haul frieght and/or do some advanced intructing in it.