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Of those two, I would lean towards the Z3. That generation of SLK was regarded as being pretty soft (as roadsters go). The BMW (particularly the 2.8) outperforms the Mercedes pretty handily if that's something you care about.

Pros/Cons from edmunds:

1999 Z3
Pros: These are some of the best cars available. Great engine choices, superb steering and brakes, and reasonable prices make Z3 cars stand out among offerings from Mercedes-Benz and Porsche.
Cons: Limited trunk space means that you will always travel light. Small gas tank means that you will stop frequently for fuel.


1999 SLK
Pros: Good looking and spunky, this is the only convertible on the market to feature the all-weather protection of a retractable hardtop.
Cons: Performance lags behind the BMW Z3 and Porsche Boxster. Cabin is uncomfortable for exceptionally tall people.


There are a few other roadsters with similar used pricing from those model years. I'd take a look at the Miata (actually less $, you could go newer), S2000, Boxster, or even the BMW M (a little more $).
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