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. Leather seats are really nice.
Pricing picks
$4500, a bit of wear and tear but cheapest by a long shot: http://www.carsales.com.au/private/details/Alfa-Romeo-Spider-2001/SSE-AD-4145736
$6990, cloth seats, black and white interior, very cleaned up, 109000km: http://www.carsales.com.au/private/details/Alfa-Romeo-Spider-2003/SSE-AD-4137643
$7000, leather seats, black and white interior, 125000km: http://www.carsales.com.au/private/details/Alfa-Romeo-Spider-2001/SSE-AD-3967786
$7400, great red colour, electric roof, 94000km: http://www.carsales.com.au/private/details/Alfa-Romeo-Spider-1999/SSE-AD-3964704
$7500, red and black interior: http://www.carsales.com.au/private/details/Alfa-Romeo-Spider-2002/SSE-AD-3992965
$7900, lovely red interior, limited Millennium edition, looks well kept, 175000km: http://www.carsales.com.au/private/details/Alfa-Romeo-Spider-2000/SSE-AD-3855731