well yes, Mr G, it happened to me once. Bought a half share in a Chipmunk in the 80s. It was the most expensive 20 hrs flying in a year that I've ever done, either before or since. Most of the time it was being worked on for ADs or cylinder head problems (we spent 3 months searching for a new cylinder head for it).
The flying qualities of the machine were never in doubt. However, the non-bottomless nature of my wallet & Mrs Poet's protests won the day and it went to a better (i.e. more well-heeled) owner in the end. Then of course the value of them shot up after we sold it. Isn't life just one long party?