So now that I've got a good and proper car, I'd kinda love another one to drive more enthusiastically...

An Alfa Spider looks really pretty, and I really love the convertible look. I can't afford a Merc CLK, but the Alfas are beautiful. Models from the early/mid 2000's are pretty cheap.

https://en.wikipedia.org/wiki/Alfa_Romeo_GTV_and_Spider

The 1998 facelift is where it's at, identifiable by a chrome frame around the front grille, and color-coded side skirts and bumpers. From 2000 onwards, there was only the 2.0L T.Spark and 3.0L V6 24V engines, for compliance with Euro3 standards.

Cheap models can be had for $4500, while a nice one is around $7500. This gets you a 2.0L Twin Spark engine putting out 114kW, and 0-100km/h in 8.4 seconds.

Power roof is optional.