My experience may be atypical (in fact it's not even quite over yet).
The hook: I found a '76 150M, 480SMOH for $10,000.
The gamble: It had been sitting in the weeds for two years, and was becoming a "parts plane." Among other things, it had been robbed of it's battery, vacuum pump, wingtip strobes, and brake calipers.
The payoff: I put some fresh fuel and a battery in it, and it fired up on the third revolution.

I got lucky, in the 1-1/2 years and seventy hours I've flown the plane, I've had no engine troubles at all, and the compressions and oil consumption are excellent!
My first annual was about $3,000 (replacing a lot of missing items), and I've spent about $5,000 more on the radio, intercom, interior, windows, etc. The only thing it needs now is paint, which I had lined up to do (for $8,000).
Recently, my wife and I bought a 172, so my 150 is for sale. If I can get $18,000 for it (which I think is a reasonable expectation), I'll essentially have flown 70 hours for "free" (not counting fuel, insurance, etc.).
If I had painted the airplane as planned, I'd have about $26,000 tied up in it, which is a little high, but well within the value range of a 150M.
I guess to answer the question... yes, it can be done... and you don't even need to take the gamble I took (in fact, you probably shouldn't).
There are some nice, flyable airplanes out there for less than $20,000 (look at the club classifieds).
Some advice: when you buy, buy in the winter... when you sell, sell in the spring. that alone might net you the one or two thousand dollars you need to break even.
Good luck!
