I work at home all the time so I have a laptop that I have to lug back and forth and it's a huge pain. Literally -- I think carrying that 20-lb. thing in and out of the building, including a huge flight of stairs, has aggravated my chronic lower-back pain (I'm usually also carrying a purse, my lunch, a bottle of water, etc.). I've started taking the elevator when I'm carrying it up in the morning.
I've seen people using those rolling briefcases, but I haven't gone that far yet.
It probably has aggravated your back pain. Have you considered trying a back pack made for laptops? If you're carrying that much weight, it might help your back to keep the load balanced. A back pack might do that.
Every once in a while, I get tired of carrying a back pack, and I try to use a brief case, messenger bag, or something of that nature. I just can't hang one of those off one shoulder; the way I'm built, they just fall off my shoulder.
Instead, I have to use a strap that goes across my body, but when I do that, it doesn't take very long before my back starts bothering me, and I figure it's because the load isn't balanced--and I'm not even carrying a 20-lb. laptop, just lunch, reading matter, gym gear, etc.
I don't want to go to a rolling briefcase. The Philadelphia sidewalks don't seem to be conducive to wheeled luggage. Even when I travel with a carry-on with wheels, I carry the carry-on to the taxi or train station!
Oh, and, typically, things are not going well with setting up my coworker's new laptop. Among other things, there is a particular application that she needs (eventually everyone on our team will probably need it), and it wouldn't work on her new machine. The guy from Desktop Services told her, "Oh, we don't support that."