Another vote for looking at the big picture (condition/maintenence), but also gotta add..
Recall the various quirks of the design! My first VW Corrado (it was a `92, 1st year of the VR6), I was stoked to find one with less than 100K on the clock. Eventually learned that early VR6s have timing chain guide problems. Shoulda bought one with 150K..by then, one without bent valves has had that job done. At least the OO (non-enthusiast lady doctor in Panama City, FL) was scared enough to do have the dangerous part of the recall work (fuel rail) done, but not the PITA one (heater core). I actually paid my favorite shop to do that one..I've made the mistake of helping a Corrado buddy take a dashboard out of one once, and I'll trade gold for blood eight days a week never to do it again. 
My buddies with 1st gen Miatas all seem to have some sort of crank pulley story, and every other car guy I know who drives older cars has similar stories about the particular things that make us say, "they all do that". 
Drew, one last comment, OK?
I consider myself very lucky that my own SWMBO (dammit, the girl still won't say yes!, but she ain't exactly left the house yet!
) grew up poor, and considers "high mileage" used vehicles as a normal part of modern life. Some of the problems she's had with her 150K 1992 Olds Bravada, she's noticed I don't have them with my 230K 1992 VW Golf. Now that she's shopping around a little, she's asking questions a lot like my own about a car. "Do you have mainentence records?", and "Is there a website for people who own these things?"
Ironically enough (especially considering my irrational hatred for all things related to Stupid Useless Vehicles..
), I'm trying to convince her to keep it. She's spent so much money getting it "sorted out" (lightly used transfer case/bunch of U-joints, and I replaced the leaky remote oil filter hoses) that it will probably run pretty good for another two or three years. Only problem now is that the electrics are getting weird. All that fancy interior lighting switched on, and wouldn't switch off a couple of weeks ago..we spent about an hour taking all of the light bulbs out so that she wouldn't have to worry about a dead battery. The damn thing hasn't burned to the ground from a short yet, so IMO we're still "ahead of the curve".
How can it be a midlife crisis, when I've driven sportscars my entire life?