Hi Strelnik
Well let's start the ball rolling then!
What you're going to get from the forum are lots of biased answers from people just like me

who love "Their" particular car! so here goes for mine:
I suggest a 300SL R107 facelift ( 86-89) and if you can find one - a Euro model possibly with a stick-shift if that's your choice.( I said I was biased!!)
Reasons:
- Seems that in the US the Euro 107 models hold their value better though they come at a premium to start with.
- The Euro models ( 300SL espcially) has better performance compared with the standard imports.(Less emmission control and no CAT)
- The Facelift ( 86-89) 107 has ABS,a better engine, improved ride, better brakes, plus loads of little things.
- An open top is FUN FUN but with the hard top you can use it in the winter as standard coupe.
Against:
Can't think of any
Cheers
Jim