I've owned both a 92 300TE (current driver) and a 92 300TE 4-matic (sold long ago). While I absolutely love these cars, I'd be hard pressed to recommend any MB of this vintage to someone who isn't a solid DIYer.

In fact, I did once recommend a 91 300TE to a close family friend who isn't a DIYer, but had the bankroll to pay for all the repairs (ortho surgeon). He loved the car and had a good ownership experience for 3 years, but decided to sell it and get a new car (non-MB). If he hadn't had the $ to pay someone else to fix it (and not much went wrong, mostly routine maintenance) he would have seriously questioned my sanity in recommending the car to him (a clean, 60k mile example with records in Vancouver, BC).

I'd never consider a 4-matic again, of course, but I would not even worry about the self-leveling suspension. It just has never failed me or given me trouble ever. If it starts to ride hard, I'll just replace the spheres. No big deal.