Audi TT (first gen)
Porsche Boxster (986, first gen)
Mercedes SL500 (R129, '96-'00)

I don't know if I'm comparing different fruits here, but based on market value, the cost of buying any of these cars is about the same. I'm seriously thinking of selling my beloved '90 190E soon and that should give me some cash to offset the purchasing price of a replacement car. I have two cars, so I'm not in a huge rush to get a replacement car after selling the 190E. Right now I'm beginning a "scratching the surface" search into another car. Originally I was set on getting a '96+ R129, but now I'm infatuated with the Boxster and only recently the TT. I think I'm fixed on getting a roadster sports car. No more sedans or "practical" cars. I already have a Volve 240 wagon to do my "dirty work."

What I like about the M-B is that I'm familiar with ownership and maintenance. I know the R129 is leap years and many classes ahead of the humble 190E, but having done some research on this car already, I think I won't get too many surprises in owning one.

The Boxster, on the other hand, I heard is expensive to fix. Cost of ownership is a bit more expensive, but then I need to confirm this. Owning an R129 is just as expensive, I'm sure. Also, I've no clue on how to buy a Boxster, much less any Porsche model. Pricing for Boxsters is a bit weird. You can find a great deal on one model year and on another model of the same year the price is high. My budget for now is limited to the '98-'00 model years.

I really like the Audi TT. The first gen has held up in style and certainly has aged well. Again, know nothing of Audi TTs, but I'm begining my research. I like it because it's probably the least expensive of the three when it comes to later model years. I can probably get an '03 for what a '96 SL500 or a '98 Boxster costs. Plus, it's great on gas I've read. That's a huge factor, but I'm willing to go with a Boxster or R129 if I can find a great deal.

So what would you guys get?