2003.5 600CL; 94 e320; 1985 500 SEC; 1985 300D Turbo. Many others over the years ...
In 1988, my mom bought her first MB (an 85 300 Turbo D). Since then, I have asked for only one thing in her will, and it has been promised to me In late 93, my dad bought a new 94 e320, which I now own (more below). A few days after he got it, he asked me to drive him to the airport. Then and there, I knew I had to have it. The first of my own was a 1987 300 SDL. Awesome car mechanically, but I have to say that for an S Class, the seats were not up to par (although the car was well maintained ... LOVED the way it drove). A few years later, I bought a 1990 560 from a member of this forum (on eBay, no less). My skepticism was promptly eased. I still have her, still drive her, and occasionally pester the guy who sold him to me for free advice. Next was a 2002 s430. Wicked mechanically, but the interior was no match for the SEC (nor is the interior of the new S class cars IMHO). My ex got our SUV in the divorce, and with 3 kids, I knew the S had to go (sniff). Got my first new car ever: a 2008 350 GL. Again, a mechanical marvel, but not only was the interior uncomfortable, the electronics were downright ass-backwards, counter-intuitive and just plain annoying. Oh, and it malfunctioned so often that MB paid me to take it back. Then last year my dad, who had maintained his e320 well mechanically but let everything else go to seed, told me he was going to give it to Goodwill. Told him I'd give him the value of whatever the tax benefit was (a pittance), and this is now my new project. Trying to turn her into something I can take to the track. So far, so good!