This is very true.
As far as years, the 993 prices are very high, I think 996 S cars are good value right now - follow up on issues like a DME, IMS, clutch/WP (hopefully when IMS done), and you can have a reliable car. The 997.1 is a little nicer, and still reasonably priced, but still has IMS issues. '05 was the more failure prone single row bearing, with an upgrade for the '06-08 cars to the double row bearings that have a much lower failure rate, however, those newer bearings are not serviceable.
I've heard 8-10% failure on the early single row bearings, less than 1% on the dual row. I think the 997.2 cars fixed the issue and failures are much more rare.
As someone who drives and works on older cars (and newer

), you should buy a modern car if you can not work on the cars yourself. Next best is a good indy shop. They can save 50% or more on dealer service costs, even on newer cars that are just outside warranty coverage. However, as Michael mentioned, there is still a lot of care and feeding that must happen with older cars. If it's a toy, no worries. When it breaks it can sit. I wouldn't recommend it as your only car if you're paying to have it fixed.