Jasony

Hi,
So I joined here a couple of years ago and was looking to replace my older Lexus with a newer MB. Long story short, warranty called to me, and I bought a new leftover dieselgate Volkswagen TDI. It's been a great car, I've been very happy with it, but I'm starting to get the itch again for something nicer. The problem is that I don't know what I want, and well, I probably should stick to a budget... I live in snowy climate in Ohio, and I need a daily driver. I also want a fun car... Some of these Mercedes could check both boxes, and some would require me to get two cars...

Currently in my garage--

2015 VW Golf Sportwagen SE TDI. I bought it new, now 18 months later, I'm sitting at 51k miles. Fuel economy is great, torque is nice, and the car itself has been reliable and troublefree... Ish. I bought it with the expectation that it wouldn't be perfectly reliable, and it hasn't, but its not left me stranded, so thats good. It's a nice car, and it fits a lot of my needs in a daily driver. I'm just getting a little bored, as I mentioned. It's financed, and I still owe about $11,000 on it. Should be slightly equitable or right around even, at worst.

2005 Acura MDX Touring. It's dead nuts reliable. Goes through the snow like nothing. Starts every time. Just does everything you'd expect. Not a superstar, but if I were taking a cross country road trip today, this is the one I would take. It just will not break. It's been in ohio forever, so its got some minor rust, but its been garaged since new, and well maintained.

1996 Ford Probe GT. I've had it since it was new. I have 23,000 miles on it. It's worth about $12 bucks. I love it, and I'll have it forever. It's my fun car, but its kind of to the point now where its not as much fun. My 4 cylinder diesel station wagon will absolutely annihilate it in just about every aspect. So now its more of just a weekends and local trips only car. It's been in the garage under cover since November. Never been in snow, and its been rained on one time. It's legitimately a time capsule car. Unfortunately, I was young and didn't stop to think that "saving" a Ford Probe might not have been the greatest use of time and money. But here we are. Again, I love it. I'll never get rid of it.

2017 Chevy Traverse awd. Its the wifes. Leased it, its a car. It does well in snow, and it hauls our kids around. I really dont care about it. Lease is up at end of 2019 and she will probably just want another Traverse. IDK...

So with these cars, The one I'm curious on replacing the VW and/or the MDX.

I still have a thing for the bluetec E320. Idk why, I just like the torque of the diesel and the features of an E-class. Get one with 4matic, and I could probably replace the mdx and the Golf.
I want an SL500. The old 90's style. I've loved those since they came out in 1990. I had a poster of one in my room. I just really have always liked them, and now they're pretty cheap for a decent one. Not sure what car that would replace, though...Wife doesn't care if I add to my weird fleet, but I don't really want to. Maybe an SL and an e320 and replace the Golf and the MDX?
E55 AMG. Because they're just badass.
2007+ S-class. I don't know much about these, other than it would be a great highway car, and I have a long commute. Thats how I got 51k miles in a year and a half.
I have garage space, and I have some mechanical ability.

I'm open to suggestions or constructive criticism.