Most of the time, you'll be driving on light snow that's falling while the trucks are out plowing. So there's a good chance you'll be on mostly pavement with the centers and curbs with small piles. The only time you're really driving on a lot of snow is when it starts coming down hard (or for a long time) and the plows can't keep up. Normally the county or state will take care of the highways, your local city takes care of the main city roads, and the rest (neighborhood, businesses, etc) is done by private plow companies hired by that person. When it's really coming down and there is actual snow piled up on the roads, many people are also driving much much slower. If it's rush hour, it'll be common to see people driving 30 mph on the way home, if that.

Definitely wear some warm waterproof gloves and get a soft brush to be able to wipe the snow off your car (windows, mirrors, hood, roof). Don't be one of those guys that doesn't wipe their car off; all that snow flies back at the person behind you. Get yourself an ice scraper as well in case your windshield gets icy when it's parked (and you don't want to hilariously snap your credit card in half).

Get some good windshield wiper fluid and fill up your tank. When you're driving on the roads and it's a gray/brown slushy mess, that gets picked up and slung back at you from the tires from the person in front of you (like the rain on a wet road). Well the dirty mess just smears on your windshield, so you need a good fluid (that doesn't freeze) to be able to clean off your windshield while driving. I had the experience of my washer tank running out and literally could not see out of the front window. I had to stop at the next nearest auto store if not it would have been impossible to drive the 50 miles home....

 

That's what I'm saying, but I've been advised against getting all seasons by basically every Mercedes Benz service department that I've called, no real explanation why.

So I've been deliberating over everyone's input, which I very much appreciate, as well as doing my own research. I've been able to narrow it down to 3 tire types:

Michelin Pilot Sport All Season 4 - 265/35/20 Front, 295/30/20 Rear
Pros:

• I watched
  this video
  on Youtube that compared the Michelin PS4S Summer, PS All Season 4, and the Michelin X-Ice Snow all on below-freezing weather with plenty of snow. From my understanding, the X-Ice Snow tire is a much more hardcore snow tire than the Michelin PA4 or PA5 or the Pirelli Sottozero 3. With that said, the Pilot All Season 4's performed very similarly to the X-Ice Snow and I imagine that the difference between the Pilot All Season 4 and Pilot Alpin 4 would be even smaller than what was shown on the video.
• I don't think I'll be driving on actual snow like the above video, as mentioned earlier I'm living in Boston where from my understanding, the city does a pretty good job of clearing the roads of snow on snow days. So if I'm driving mainly on dry or wet conditions that don't necessarily have a need for snow tires, and the video above shows a marginal advantage to snow tires when driving on snowy conditions, then I'm not sure that I see a huge advantage for winter tires in my case.
• Good reviews on TireRack
• Exact same tire sizing as the factory summer tires.
• I can use these into the summer if I wanted to.
• Least important, but still an advantage: cheaper at $1284 for the set of 4.

Cons:

• TireRack is backordered on the rear tire size and I'd have to go to another supplier to find them on the timeline that I need it in (under 2 weeks).
• I'd hate for this to not be enough in Boston winters, I feel like it might be fine but I really don't want to regret buying all seasons a month after installation and spending another $1500+ on a winter set for a leased car. I feel like winter tires may be the more sensible option, but all seasons seem tempting and convenient.

Michelin Pilot Alpin 4 - 265/35/20 Front, 295/30/20 Rear
Pros:

• Strong winter tires, I know I'll be good driving these regardless of the road conditions.
• Exact same tire sizing as the factory summer tires.
• Pricing isn't bad, $1569.

Cons:

• Need to determine shipping from Alloy Wheels Direct.
• Can't drive on them when temperature goes above 50 degrees, so I'd be forced to switch back to my P Zero summers.

Pirelli Sottozero 3 - 255/35/20 Front, 295/30/20 Rear
Pros:

• Good winter tires, not sure how they compare against the Michelin PA4 but I suppose you can't go wrong with either.
• Readily available on the sizes mentioned above off TireRack.
• Price is fine.

Cons:

• I'd have to go narrower on the front to 255 instead of 265, I know it's not a big deal but I suppose it's still a con.
• Lower speed rating.
• Reported to not last more than 7k miles, which is unfortunate.
• Can't drive on them when temperature goes above 50 degrees, so I'd be forced to switch back to my P Zero summers.

That's kind of where I'm standing now, the only reason I'm considering the PAS4 is because of the video I linked on top. I was impressed by the performance, but will be watching more videos to make a better decision. Any input is appreciated. Thank you all!

 

Very insightful, thank you. The question becomes how much has all season tire technology improved since this 2009 video? If you see the video I linked in my previous post, you'll see very different results on the Michelin PAS4.

 

Anthony, no one drives on a hockey rink! Tire compounds have greatly improved over the last several years that reduce the advantage of dedicated snow tires on ice and cold temperatures. Time to get updated. Look at this YouTube video: (You'll see that the differences in performance are just not that dramatic anymore). I lived in Cambridge Mass for 8 years. Boston snow removal is great (unless you get a monster storm at which point nothing moves). The need for dedicated snow tires in a modern city is just not that great anymore. When I was in CT, I used European cable chains if the conditions warranted it (basically ice). When I lived in Cambridge, I had studded snows on my Camaro (I don't believe that Massachusetts allows them anymore) which were really good on ice.

 

1. why aren't you considering keeping the car after your lease goes out? who knows if they will even offer a v8 E63 again... and certainly not a wagon. (your car's residual might be a lot lower as to what the car would sell for at that point.)
2. I have a set of 265/35R-20 Dunlop SP Winter Sport 3D XL squared all the way around on my wagon. With this setup I can go anywhere until I get hung up because of ground clearance. I've used versions of this tire since my days with my W211 500 wagon. Many a ski trips from NYC to North VT without ever and I mean ever having an issue of not being able to drive the car comfortably in any condition...They are reasonably priced and work great on the car. In Boston, you'll want to journey out and beyond the city... New England is wonderful in the winter. Enjoy it.

 

I was able to get this setup from TireRack for around $1600 last year. The wheels are nothing special but they look good and they're for the winter so....
I went with Yokohama winter tires and I'm happy with them. They are wearing fine and while you loose some steering feel they don't get all squirmy under hard acceleration like I've felt with some other winter tires. 19" too. Better for those winter damaged roads.

 

Problem with most cheap wheels is that the offsets are wrong. Our winters are too long to have the car look crappy for that time. We only keep these cars for 2+ years so extra wheel sets weren't worth it for me and the dealer swapped the tires quickly and we had wheel insurance on the forged rims. Car looks how I like it and handling is best that way.
Plus Draggy showed 3.28sec to 60 with the Sottozero's. Good enough for me

 

Didn’t mean to offend your setup in my last post!

Car looks great but the front could use some spacers

 

Yes I agree haha but I'm fine with it for the winter months. I customized what Tire Rack suggested a bit. I went with wider tires and a different front wheel width so I'm not sure how that changed things. They may have had one that fit better. The spacing is probably fine on the non-amg's and e43/53 because of the normal front fenders.