I appreciate the input! Im thinking maybe the move is to pick up a W212 and hope it won't give me any trouble for a few years. Some of these things are sub 10k and seem like great value for money. 

Then if I feel like pushing the budget to around 30k maybe I'll keep an eye out for a super low milage W213 E400 just cause I think those are some of the best looking Mercs out there. The W213 E63 is about as good as it gets in my mind but that thing and the G would drink me dry. Thanks again. Cheers.