My mom has had a 2005 Chrysler Crossfire since new, so I've learned a decent bit about the first-gen SLK's. The Crossfire is an R170-chassis SLK320 in drag, built by Karmann.
The R170 first-gen cars seem pretty reliable with just routine maintenance. The convertible top may eventually need some of the hydraulics repaired as it ages, as the seals can leak. The Crossfire has a soft top vs the SLK's hardtop, and the rear window glass is glued into place. It will eventually start to fail. Your engine options were a supercharged 2.3L inline-4 (SLK230), naturally-aspirated 3.2L V6 (SLK320), or supercharged 3.2L V6 (SLK32 AMG). The Crossfire never got the four-cylinder.
I think the 230 could be had in manual-trans form, the 320 can definitely be had as a manual, and the AMG is automatic-only. They all got recirculating-ball steering which is easily the worst part of the car IMO. It provides rather poor road feel - this is not a BMW or Miata in that regard. Regardless, it's fine for commuting and back-roads cruising which is where these cars excel. I would almost be inclined to recommend the automatic transmission no matter what, as the manual in my mom's car is pretty clunky and truthfully not all that fun. Mercedes makes a very good, durable automatic and these are a 5-speed auto if you buy one so equipped. The 230's are pretty slow, I had a friend in college with one and it was underwhelming.
There are known issues that crop up with various relays in the engine bay, they are located too close to the exhaust manifolds and fail over time. Easy to repair though, with almost no tools and about 15 minutes' time.
The car has a chipped key as with anything else of the era, and the solder joints in the immobilizer computer will fail over time, again due to heat. This means the car won't recognize the key and will refuse to start. A new computer is a few hundred dollars.
We had an issue with the alarm system's backup battery failing - it is located in the siren, and when it goes bad, the alarm will go nuts. Constant flashing hazards, things like that. You can unplug the siren and just leave it that way if you want, or replace the siren. We used one from another same-era SLK, I think.
They seem to be pretty good cars, they are definitely GT cars and not the most raw, connected sports cars in the world. I borrowed mom's for a few months while she was recovering from knee surgery and enjoyed it as a commuter/cruiser.