When you start looking at this age range, the exact model becomes less important. You should think about how much time you want to spend every week on repair/maintenance; that will be a good indication of how old you can go. The older you go, the more frequent attention the car will need (so… repairs will be more frequent but easier when compared to a new car). You can also expect poor fuel economy.
If I were looking for a simple-to-repair car, I would look for something with the following features:
Electronic ignition. You do not want to mess around with points; even the older electronic ignition systems were pretty reliable (and the ignition modules were cheap enough that you could keep a spare).
Either non-computerized carburetor (so… prior to about 1982) or non-first-generation electronic fuel injection (about 1988 or newer).
Rear wheel drive (prior to about 1985; after that there are a number of front wheel drives that have held up pretty well). I wouldn’t get a four wheel drive unless you need it or enjoy rebuilding driveline components.
Relatively simple emission controls (so… if you see 10 miles of vacuum hose under the hood, you might want to pick something else).
Front disk brakes
I would look at models such as:
Late 70s or early 80s GM full sized (caprice, 88, etc.) with the 8 cylinder motor
Late 70s or early 80s GM or ford full-sized pickups or vans
Early 90s Ford escort or similar (I know… this doesn’t meet the criteria above and is considerably more complicated, but they seem to have good longevity and are still comparatively easy to repair).
When new, some cars from 30 years ago were a lot better than others. After 30 years of use, though, I think you will find that they pretty much all have similar numbers of problems.