If you can find a '92 or '93 190E with both the factory Sportline package and a 5-speed manual, that might be an optimal budget alternative. See http://www.peachparts.com/shopforum/showthread.php?threadid=29894

The 190E Limited Edition (of which 700 were made in '93 only) had the factory Sportline, quicker ratio steering, a smaller steering wheel, special wheels with 205/55/15 Z-rated tires, 4 place sport interior like the 2.3-16V but with black leather with red piping and inserts, carbon fiber dash, etc. -- however, the transmission is the 4-speed automatic rather than a manual. Given the limited production, they are very hard to find (there are currently two listed on Autotrader) -- I got one for my daughter with 64,000 miles for under $12,000, which I thought was a real bargain and well within your price range.

Another alternative is the C36 (tho it does not have the interior room of the 400E, it will blow its doors off as well as leave it in the twisties) -- the earlier versions are now down in the $20's, tho the '97 with the 5-speed transmission is, IMO, more desireable. You'll pay a bit more for a Starmarked example, which might be worthwhile as insurance against replacement of expensive AMG-specific engine and drivetrain parts (tho there's no reason to believe that they are susceptible to failure).

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'98 C43 AMG
'88 420SEL
'93 190E Limited Edition (including factory Sportline package)