What is the best chalk + bag combo for keeping my hands dry and callous free while weight lifting?

You could try liquid chalk: link:Tite Grip

I don't know if it's suitable for lifting, but you could look at using a traditional rock climber's chalk bag. They're available at any store that supplies climbing equipment (e.g., REI, Eastern Mountain Sports, etc.), and can also usually be purchased at climbing gyms (e.g. Planet Rock) or online. Climbers typically hang them on their harnesses; when I was into climbing, I wore mine on a separate belt for convenience, and I'd imagine you could do something similar.

If you go this route, here's something else to try: put your chalk inside the foot of a nylon stocking, tie it off, then put the stocking inside the chalk bag. This makes it easy to squeeze chalk onto the palms of your hands and your fingers, without having it go all over the place when you pull your hand out.

There's a palm-cushioning gadget, which attaches by elastic finger loops, called the Gripad. Here's its site: http://www.gripad.com/

There's a palm-cushioning gadget, which attaches by elastic finger loops, called the Gripad. Here's its site: http://www.gripad.com/