I have no patience for this kind of thing. What's likely to happen is I'll buy a $23k airplane and sell a $15k one, just because I don't want to spend too much time looking around up front or holding off offers at the end.

I recently sold a Triumph Bonneville which, it turns out, is a very price sensitive item. At the first price I got a few emails from scammers but nothing serious. After two weeks, I dropped the price $200 and my email box filled with real buyers. Would it have sold eventually at the higher price? I'll never know. But I didn't have to haggle with the buyer, which might be a bad sign....

Join the Cessna 140/170 club and learn the market if that's the direction you want to go. I think you could get a 170 for about the same $$$ and get more utility out of it. Type clubs are the way to find out the ins and outs of these old airplanes. And, I wouldn't take for my tailwheel experience, I think it's the best training any of us can get. There's nothing like going out and flying pattern after pattern in the cool of the day.

Man, I'd love to know where the mid $20K 170s are hiding. We looked for a few of them and there's not much out there for less than $35K.

140's are clustered in the 20's, 170's in the high 30's - low 40's, 180's in the 70's, and 185's are scattered upwards from $120k.

With the ridiculous exception of 185's, the market reflects utility pretty well.

The 185 is a working airplane in Alaska. $$$ = utility

If relative price reflects relative value I'd rather pay more and get better. A 60 year old airplane that has had a ground up restoration, well documented and carefully inspected, should return a lower overall cost of ownership and far fewer ownership headaches. With a delta from crap to pristine of $10k or so it's worth the difference in my opinion.

Pristine is hard to find, and they're often priced really unrealistically- like $35-50K (or in the case of a 140 have crap useful load). And there's plenty of crap to be found for $15 but occasionally decent for $15. Probably not much harder to find decent at 15 as pristine at 25.
Problem is that the market is mostly decent, asking 25.

Deals are out there; estate sales, health reasons, maintenance reasons, airplanes racking up hangar/tiedown fees not being flown. Some sellers just want out and some will hold on until the bitter end.