THOUGHT ID POST SOME ANSWERS I GOT FROM ANOTHER FORUM:
w210 E55 is a solid car. probably don't have any problem except it just looks old, but you can mod it some and make it look pretty classic. the last year is the best.
02-04 C32. supercharger won't be the problem with this car. i don't think anyone on the board has actually blown their supercharger. the thing that will need replaced is the supercharger clutch bearings and those are cheap. the crank position sensor which is cheap as well and then there are the common problems with the w203 such as powerseat draining the battery. all the problems are pretty much all listed in the forum and most of them can easily be DIYed.
w209 clk500 or 55. again, solid car. the later year the better. some common issue shared with the 203.
the crank position sensor are a problem common on all MBs.
B6 S4, from what i have seen. some people seems to have electric issues for ignition wirings. other than that...good car is you want a decent power V8 with 4wd. but the interior room is crap.
E36 M3, clean ones are hard to come by. unless you want a project car. it's not worth the hassle.
E46 M3, you have a 330Ci. i'm pretty sure you are aware of E46s' problems.
MB depreciation is ****, but the CLK500 and w211 E500 in same condition as the C32 will actually cost more. all depends on what year and $$ you are looking for.
I understand the 4.2L Audi motors are quite the pain when it comes to timing chain and tensioner issues. Motor out procedure. But arguably the nicest interiors of the three mainstream German manufacturers.
I would suggest the c32 or e55, why? they got good brakes and engines that can take some punishment. Take a look at the 210 e55 picture threat they can look pretty badass. love the v8 from the E55amg handles pretty good for a big car and it sounds amazing, for the more sharp cornering and maybe track driving? c32. the w211 is a nice car to, but it's a whole different kind of car it's more like the grown up man's car, still got plenty of power. Test drive a c32 and try an e55 again, and decide everyone has a different opinion on how a car should feel like driving it's up to you.
Sweet! Great info from you guys! Thanks! Yes, ill take a c32 for a drive. Regarding the W210 e55, I know the 2000-2002 is a better version than pre-2000. But I prefer the pre-2000 side skirts better. It looks more slick / smooth / flush. What I also realized is that the e55 doesnt have a limited slip dif. Wtf. When I drove one the other day, in the dry, I noticed the traction control light kept flickering to aorox 100kms. If it had LSD, is imagine it would pull even harder.
myself I prefer the before face lift look also, they are pretty reliable make sure transmission has been serviced right.