I'm 31, on my 2nd Cadillac, 2nd Deville. Got the first one, a 91 back in 2000. Lasted about 2 1/2 years and then started eating my wallet in repairs. Decided to write that one off, got my 1995 and couldn't be happier.
The 95 has been a great car, and while I have put a lot of money into it, it is easier to stomach the repair bills this time around because I have more money (a change in jobs made it easier to handle this aspect) now than when I was driving the 91, and the 95 is perfect inside and out. It just looks so damn good I don't care about spending the $ to keep it decent.
I have already told myself that the next one will be an Eldo, love that design from the late 90's/early 00's. Since I've already had two Devilles, I think it'll be time for a change when I buy another car in 2 or 3 years and the Eldorado will get the nod. After that, who knows? I'm really stoked about the 2006 DTS, so after the Eldo I'll probably try for one of those, but I am getting way too far ahead of myself here.