Don't buy a MB, keep the Lexus.
I wouldn't touch an early W140 with a 10ft pole, unless I wanted a project car and had a few grand burning a hole in my pocket. 1997 and newer only.
No offense but your old 380 needed a timing chain, other than that judging by the pictures was in good shape, you should have fixed it and kept it. That 300SE isn't going to be any different. If an $800 TC job scared you into selling it...no other older MB is going to be any better.
What are you going to do when that S500 needs an evap core? SLS work? Window regulators? LCA bushings? Thats a fine car but your going to drop a few bucks a year taking care of it. Heck it probably has damn near 200k on it so you really should pop the valve covers off and take a look at that chain. If it were my car I'd replace it along with the guides. Don't forget the wiring harness, if that hasn't been done yet its way past due. MAF's also seem to fail every so many years, $300 a pop X2 on that car.
Cheap to buy, doesn't translate to cheap to own.
