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My friend, these guys know their SLK's...much more in detail than I at this point in time. I gotta tell you, there is so much to this car, and so many intricate variations from year to year, that the best thing you can do is read until you turn blue.
HOWEVER, I know my 350's. Everyone has their preference, and I gotta admit, after doing a good few test runs with the SLK, the Z feels like I'm riding in a cardboard box. And my other car, the BMW...well, she's toasted. But that's just my inane 2 cents on that.
The 370z in my opinion, is nothing short of an abysmal failure, both style wise and in regards to the engine. Why do I mention this? Car dealers, at least I know for sure here in America, will NOT cut the price of new vehicles. There are many reasons for this, but for the sake of time, I'll skip the business lesson. Used cars however are a different story. They'll be slashing all used models with the debut of the 370, which at least in my area, only came out a few short months ago. Bottom line, 350 z's, roadster or not, as long as its used, will free-fall price wise. Give it some time, and they'll keep dropping. The only example contrary to what I'm saying might be fairly new '08 roadsters, that only have a few miles.
Try as you might, you'll never be able to tumble in a Z (ignoring extremes)...whether a regular 350 or a roadster. Now, if you're talking about the Nismo, originally not even released here in America...then that's a different story. Sadly, from what my memory recalls, that one doesn't come in automatic which is the only way I drive. But that top end Nismo...yeah I'll admit, that one got my blood pumpin.
If I could throw in another 2 cents (lets make it 4 cents all together, haha), the 350 to me is a high school ride (thats just me). The SLK is, to me, light-years beyond. Can you sense my favoritism? Hahaha. Also, as I'm sure you've noticed, the back portion of the roadster is slightly different than the normal 350's...an alteration I'm not fond of...compensation for the convertible top.
To reply to your 4 points:
1.) I wasn't happy with the internal quality of my 350Z. I had issues with the nav, the adjustment piece to my steering wheel was somehow defective, and I HATED how the back looked. The positioning of the speakers...I don't know...I just hated it.
2.) The Z didn't cost me much to maintain. But to be honest, what extra I foreshadow spending on the SLK, is worth it by far.
3.) Two totally different styles. That mate, is your call.
4.) Just to throw this out there, the 350Z doesn't have 350 horsepower...you might have already known, but I flipped when I discovered that.
Hope something helped! Good luck on the decision.