I love the older Craftsman with the raised side panel. I got mine in the mid 90's and still use them to this day. I keep them in a roll and take them with me when I'm going to be off grid for awhile.
The Milwaukees are longer and thinner, but the box end is taller and can be seen in the below image, which gives it more surface area contact, meaning less stripped bolts.
Also, the open end has groves cut into the mating surface, and they work great. When I feel like I'm about to round off a bolt with the Craftsman, I generally reach for the Milwaukee and it bites into the fastener extremely well. Bolts that I always had to be really careful with, like rusted exhaust bolts, are no longer an issue if I have enough room to get a wrench on them, the open end of the Milwaukee really does bite that well.
As far as comfort goes, I still prefer the Craftsman, maybe because of the thickness or the familiarity in my hand. Also, the Milwaukees will get slippery when my hand gets sweaty, but I find that to be true with almost every chome tool.
