Date registered: Feb 2008
Vehicle: 2004 W220 (S430) ; 2001 R129 (SL500) Sport
Location: Alabama Gulf Coast--formerly Charlottesville, VA
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You started in the right place, but let me suggest you scroll through the other forums on this site. Each chassis has a designation--for example a W220 is the S-class chassis that was made from '00-'06. There are a number of engine and transmission combinations in that model run, but the body style and interiors are fundamentally the same. In this site, there is a forum for every modern chassis. You can find several versions of the C-class, the E-class, and the S-class, as well as roadsters and coupes. There are also forums for AMG versions of various chassis designations. This is where you will learn details (such as reliability and known faults as well as desirable engine/transmission combinations and desirable options to look for). Most also have a "buyers guide" in the stickies at the top of the forum.
Once you have settled on a likely body style, or even if you're still looking, go to the individual chassis forums where you will find a group of people who own those cars. They are usually helpful and knowledgeable and will be quite willing to tell you what models to consider and which ones to avoid.
This is a great place to do what you are doing. Be nice, and everyone will be willing to offer their opinions and help.
Good luck on your search.
"Don't pick a fight with an old man. If he is too old to fight, he'll just kill you."--John Steinbeck