I was in an accident in september and totaled my 2003 jag xkr coupe 
Now I cannot decide (from least t to most expensive):
- stick with dad's 1995 s320 with 300k miles (~free)
- a new jetta tdi
- a classic benz such as 280sl or 190sl (and drive it half the time, interchange with the aforementioned s320 above)
- get another jag xkr coupe (nothing newer than 2006, they get ugly imo)
- audi a5/s5
I saw an a5 yesterday on the road and thought it looked almost as good as the xkr coupe. Beautiful car. I really want the tdi version (diesel holds a sentimental value to me) but those are not available in the states :doh. I can get a jetta for half the price and tdi. And the jag - for some reason, it was a love-hate for me. It was beautiful, attracted too many old guys (chick magnet feature was busted) but because it was used (and slightly abused until I babied it), it never felt right. I love the old benz's, have a great mechanic lined up for them, they are convertible and small and so much fun to drive even if slow - but they lack the safety features and modern bells like heated seats and nice sound system. With the jetta, I'd feel too "common" (I like to be unique) and maybe like I'm taking a step back. The s320 feels like I'm driving dad's mercedes, which, well, I am - but I'm dieing to invest in the RE market now having spent the last 10 years living at home and saving my hard earned income, and the car is enourmously comfortable.
Thoughts? Features I "want" - unique, good looking, heated seats, convertible. I realize I cannot have all these without spending too much (if I could afford one, I'd get a 300sl roadster from the 50's and put in my own seats). I live in so cal, so new cars like bmw's and mbz's are fairly bourgeois. I wish I could lease but I put too many miles on the car per year (about 20k).
There are deals to be had out there now wrt new cars. I've heard cool stories about the bmw's with 0 maintenance programs, huge discounts off the sticker, or amazing lease deals. I like how they well outperform the audi at a lower cost, too, but - there's just something too common about them, too, like the jetta.

Now I cannot decide (from least t to most expensive):
- stick with dad's 1995 s320 with 300k miles (~free)
- a new jetta tdi
- a classic benz such as 280sl or 190sl (and drive it half the time, interchange with the aforementioned s320 above)
- get another jag xkr coupe (nothing newer than 2006, they get ugly imo)
- audi a5/s5
I saw an a5 yesterday on the road and thought it looked almost as good as the xkr coupe. Beautiful car. I really want the tdi version (diesel holds a sentimental value to me) but those are not available in the states :doh. I can get a jetta for half the price and tdi. And the jag - for some reason, it was a love-hate for me. It was beautiful, attracted too many old guys (chick magnet feature was busted) but because it was used (and slightly abused until I babied it), it never felt right. I love the old benz's, have a great mechanic lined up for them, they are convertible and small and so much fun to drive even if slow - but they lack the safety features and modern bells like heated seats and nice sound system. With the jetta, I'd feel too "common" (I like to be unique) and maybe like I'm taking a step back. The s320 feels like I'm driving dad's mercedes, which, well, I am - but I'm dieing to invest in the RE market now having spent the last 10 years living at home and saving my hard earned income, and the car is enourmously comfortable.
Thoughts? Features I "want" - unique, good looking, heated seats, convertible. I realize I cannot have all these without spending too much (if I could afford one, I'd get a 300sl roadster from the 50's and put in my own seats). I live in so cal, so new cars like bmw's and mbz's are fairly bourgeois. I wish I could lease but I put too many miles on the car per year (about 20k).
There are deals to be had out there now wrt new cars. I've heard cool stories about the bmw's with 0 maintenance programs, huge discounts off the sticker, or amazing lease deals. I like how they well outperform the audi at a lower cost, too, but - there's just something too common about them, too, like the jetta.