Date registered: Feb 2008
Vehicle: 2004 W220 (S430) ; 2001 R129 (SL500) Sport
Location: Alabama Gulf Coast--formerly Charlottesville, VA
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For a young man, let me suggest a late model ('00-'02) R129 SL500. It's a two-seat roadster with a convertible top that stays with the car and a removable hardtop for the winter. The combination of the M113 engine and 722 5-speed transmission is nearly bulletproof if you maintain it. The car itself is relatively simple to repair with springs and struts for suspension rather than airmatic. The 304 horsepower will propel the car 0-60 in 6 seconds, and it has a limiter to hold the top speed to 155 mph. The '01 and '02 R129s all came with staggered 18" AMG wheels and body cladding, so they look pretty aggressive.
The truly nice part is you can get one for $18k in tip-top condition. My '01 had a sticker price in excess of $90k, but I bought it in July this year with 64k miles for $17k. The rare '02 Silver Arrow version can be had for $24k or so if you can find one. You can spend the residual on a nice cruise for your birthday. Because most of the R129 were sold as second or third vehicles, many have low miles (40k-60k) for their age.
The newer R171 SLK roadsters have folding hardtops, but practically no storage with the top up or down. They are smaller, lighter, less powerful (unless you get the AMG version), and considerably more complicated than the R129, but are "younger" than the big roadster. You can get a late model--'07 or '08 for about what you're planning to spend.
If you really want to play with the big boys, the R230 roadster is the successor to the R129. The '03-'05 SL500s can be had well within your price range. They also have folding hardtops, but have more storage in the boot as well as storage space behind the seats. Later models became SL550s, and came with 7-speed rather than 5-speed transmissions.
All of my suggestions carry a hefty insurance premium for someone your age since they are all considered high performance by the insurance industry.
Good luck in your search. I envy you the choice.
"Don't pick a fight with an old man. If he is too old to fight, he'll just kill you."--John Steinbeck
Last edited by DrJfrmLA; 12-22-2009 at 02:52 PM.