My base model/no ABS 95 has the 8.25, as does my 99 and my son's 96. My daughter's 93 Sport with no ABS has a D35. This suggests that the change is somewhere between 93 and 95 for non-ABS models.
As far as other things to check, rust is the obvious one, along with signs of abuse or damage, and otherwise, I think it really depends on taste to some extent. My 95 has been phenomenally reliable, but the tinworm has pretty much eaten it to death. The 99 has been fine too, but it's about a hundred thousand miles behind the 95, having just turned 161K, so time will tell. Each has some pluses and some minuses. I don't like the storage in the new design. If you use your handbrake, you'll like the 97+ improvement there. The later steering column and wiper controls are nicer than the 95-86 Chrysler design. I prefer the seats and steering column controls on 87-94 to the later ones, but not enough to avoid a later one in better condition. My 87 Pioneer had the most comfortable long-distance seats of any vehicle I've ever had, but both the 95 and 99 are decent.
In the under-4000 category, you'd do best, I think, to shop for overall condition and rust. Ignore the fancy options unless all other things are equal. Simple can be better on an older rig anyway, and even if you get one with no gauges, etc., these are things that are easier to upgrade or correct than a glitzy one with a bad drivetrain or serious rust.
