Date registered: Feb 2008
Vehicle: 2004 W220 (S430) ; 2001 R129 (SL500) Sport
Location: Alabama Gulf Coast--formerly Charlottesville, VA
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The roadsters you are considering are R107 chassis. If you scroll down the site, you will see a forum that is for this chassis, and most of the people who visit that site own some version of this chassis. There is probably a "stickie" at the top of the forum that is a buying guide.
I am sure there are versions of the R107 that are preferable to others. I own an R129 SL500, and there are model years in the 12-year run of that chassis that are considered preferable. I imagine the R107 is the same.
I doubt that anyone is going to take the time to write you the several hundred or several thousand words it would take to reply to your query. It's too broad a question. Snoop around that forum and narrow your choice to either a 450 or 560 and perhaps a range of MYs, then ask a more specific question. There is also a 350 version of that chassis in a few model years.
"Don't pick a fight with an old man. If he is too old to fight, he'll just kill you."--John Steinbeck