I've got a 2008 CLK 350 Sport Convertible. Lovely car. Few things to watch:
If you buy a V6 (M271/2 engine fitted to the 3.0 and 3.5) check the engine number. Google Balance Shaft issue Mercedes and you will get an engine number "range" to avoid. MB fitted soft steel sprockets for a few years and the engines required a full strip down as a result. Sprocket had to be replaced but required a complete strip down. Huge class action lawsuit in the US. £000s to fix if it happens to you. But very easy to check. Rule of thumb is avoid cars built 2005 - 2006 as they tend to have the problem engines. Late "run out" cars are generally OK as are earlier cars. But check the engine number to be sure as you could find an "old" build date engine in a newer car.
Otherwise, check the roof works. Gazillions of microswitches and motors to go wrong. But generally they are fine. Ditto all the motors that control the seats, headrests, wheel height etc. Just check it all works as fixing it can be fiddly. SRS warning light often caused by tight wire that runs under the drivers / passengers seat and up to the seat side airbags. Common fault; warning on dash. Can be fixed by re-routing the wire so it doesn't "pull" when the seat is tipped. My indy did mine for £50.
If it hasn't had it done, budget on an autobox oil and filter change every 35-40k miles. Preserves the life of the box and is around £250 from an indy.
Sport trim if you can - AMG "look" with nicer wheels, lowered stance. Sets the car off nicely.
Otherwise, search out a nice spec. COMAND is nice but does feel old-fashioned compared to new cars. But it works and I'm glad I have it. Heated seats a nice extra on the convertible. Makes it more usable for more of the year.
But generally, buy on condition and provenance. I paid top dollar for a very low miler back in 2015 but I'm glad I did. It's a joy to own and drive.
Generally they are good cars; early ones suffered a little from MB's lax approach to rust proofing but later ones (from 2005) are fine. Like any complicated prestige car, there is always scope for it to throw a big bill at you, but generally they are not known for being problematic.
Just take your time and find a good one.
If you want to chat I'll be at Benz on the Green in May - look out for me!
Final thoughts - bigger V6s suit the car better (or the super rare V8 500), but if you buy a post 2005 car, the road tax is £500 a year. Puts some people off, but I think it is worth it for the additional poke and refinement. Cars before 2005 are taxed differently and are around £280 a year I think. Check before you buy if that's a deciding factor.
Space-wise they are pretty usable. I take mine plus wife and 2 kids (aged 3 and 9) all over the place in it. South of France no bother. It's a proper four seater and decent boot with the hood up. We've even been camping in it with all the associated kit.