We're fans of this approach: we typically aim for a <10-year old entry-ish level vehicle from a "luxury" brand. Our mechanic (who is also an old friend) is an Audi aficionado, and that's what we enjoy driving, so he does the pre-purchase inspection and we're off to the races (er, so to speak). I prefer smaller cars, so the most recent purchase was an Audi A3 (manual, baby), to replace a 1995 Audi 90 Quattro.
We don't drive much (typically < 6000 miles/year, including a few long road trips, two kids in club soccer, and a handful of ski patrol days that involve >150 miles of driving), so we generally don't rack up too much in operating expenses, and it's nice to have the ride be sweet when we do have to drive. We budget for around $2K in vehicle work per year, so it's probably a wash between this strategy and buying a newer less-luxury model car, except that we get to drive a nicer car in between. Older also means lower insurance rates... Downside is I need to keep taking the keys away from the 16-year old (6-speed with a turbo = MY midlife crisis car, kid. Ride yer bike!)