I-Drive-Benz: SL500/600
Hi. I bought my 1992 500 SL brand new. I never purchased a used MB; so, I don't know whether or not your target car is within the price range you mentioned in your email. I recommend you look into the Blue Book to find the price range.
My experiences with my 500 SL has been extrememly positive. She is one of my daily drivers; she is fast and reliable and lots of fun to drive. My other daily driver is a C280, and she is also a great car. Weekend drivers are my Ferraris: 328 GTS and 512 TR.
As with any used car, you should get a mechanic to check her out. Remember, your target car is between 5 - 10 years old, so beware that mechanical operations and parts begin to show wear in the older years -- this could lead to high expenses. Make sure the previous owner respected the maintenance schedules.
Although the SL is not a high-visibility profile car like a Ferrari, expect public attention -- after all, you are driving one of MB's flagship cars, and you are young.
If you are working and are expecting advancement through your company, I recommend that you don't let your manager see you in her -- people get jealous of nice things and so will your friends/social circle -- be careful of vandalism.
When I was 19 years old, my parents bought me a brand new 1983 Porsche 911 Cabriolet. I never let people at work see me in her. People in my social/college circle also were jealous, so I made sure I was careful not to bring attention to her.
When I was 24 years old, I bought my first Ferrari. People at work never saw me in her.
Kid, you and I have the fortunate experience in that we drove some shit-hot exclusive cars at a youthful age -- it's one of the best experiences you will have -- so enjoy it, be safe, and keep a low profile at work.
Keep me posted with your purchase -- Good luck.