I looked at a Luscombe yesterday. I've flown a few of the planes on your list. Here's my 3 cents;
All of them are fairly cramped. Low overheads, narrow fuselage, small doors, and small windows. Not a good place for anyone who doesn't do well in confined places. You will be rubbing elbows, and shoulders with your pax in the side by side planes.
They are all noisy. Of course, we have headsets now to deal with this so not really an issue. Almost all of them have been groundlooped or flipped on their back. This isn't a problem if it has been repaired correctly. Plan to have an A&P look in the gear attach in the fuselage, and the top of the rudder, as well as the firewall. All of them require - how shall I say this, better than average landing skills. None of them will land and roll out cleanly without plenty of pilot attention. The Luscombe is prolly the worst of the bunch, but the Clipper/Vagabond is no picnic either. You get used to it, you are diligent, and nothing gets broke. Otherwise, reread the above mention about groundloop or flip on back.
For the most part they are marginal performers. Plan on anemic climb performance with the A65, A75, or O-145. If you can find one that's been modified with a C-85 all the better, and maybe a metal prop to improve thrust.
The saving grace, as you've mentioned is that the running costs are really quite low. I would get only liability insurance because your out of pocket is small, and if you smash it up, just plan to part out what's left. Low cost auto fuel can be used, and it doesn't use much of that. Low and slow is the plan, although the Luscombe can go about 115MPH with the 85 HP at altitude. Most of them are limited to under 100MPH.
With age comes corrosion. For all of these planes, an extensive inspection is needed for corrosion. For the Piper family of tube and fabric this usually is found in the lower tube braces of the rear fuselage where water, and gunk tends to accumulate. For the Luscombe, it's back in the metal tail cone area as well as under the floorboards behind the gear attach.
I'm likely going to grab up the Luscombe and just float around in the sky on nice days. Not for long distance, or heavy loads of course, but still as much fun as the go-fast at a fraction of the cost. Plenty of parts have to be made, and the 65HP Conti is fairly well supported, as is the C85 should you find one of those.