From a 80 280SL to a 99 SL600

[96E300D]

From a 80 280SL to a 99 600SL, how's that for some progress? Actually it's not official and I'm still doing some research on prices and practicality. After checking out on the 280, I started familiarizing myself with the SL's in general and began looking at the 86-88 560's. Problem here is that most have high mileage and the shape of all the ones I've seen in the $8000 range is not very inticing, and its purpose would be a daily driver. So then I moved on to the newer 90 - 99's and found some nice low 90's in the low to mid teens. While I had never driven one of these, I happened to remember a neighbor who has a newer SL. I called him up to get some owner information on it and lo and behold he said he was just thinking of selling it. Turns out it's a 99 SL600 he purchased at a good price, it now has 35K on it and he's thinking about the mid thirties for a price. I'm working really hard to figure out if I can make this work, or if it's the right car at this point. Initially it started out being a Christmas present for my wife but I may have to re-think this. One other thing in the mix is we have two younger kids and the other option I've just started looking at is the 2000's CLK convertables. She still gets her convertable, yet in a pinch can take the kids if necessary. Price range for these would be about the same for the SL600. I do have a question here, will the SL600 hold it's value any better than the CLK or any other older SL? I'd be interested in hearing what you think.
Matt