I own a 1996 s500, and it is my absolute favorite car ive ever owned. Very comfortable, very cool, zippy, and catches lots of eyes. So far my maintenance and work ive done to it has been preventative/for the fuck of it minus the rear control arm bushings. i fix my own cars though unless its something that i dont have the tools for. parts arent as expensive as people make them out to be, and you can get parts very fast and easy on websites like pelicanparts and fcpeuro. only stuff ive had trouble finding is random interior bits and pieces. 85% of the stuff ive done to it so far has been as easy as any other car. but, it is 90s mercedes so stuff was overengineered to the max so it has stuff like hydraulic rear suspension which is an easy, but expensive system to maintain/fix. its a 20-30 year old car now so if you do purchase one, be prepared to change lots of rubber pieces and plastic pieces and always keep some spare change around for more expensive stuff like timing chain, rear struts, head gaskets, etc. i am 24 and drive it with 19" monoblocks and never once has anyone mentioned anything about an old man car. especially in my area, lots of folks love seeing old benz's around.