Go to your local Micro Center and pick up a flashdrive to carry your team files around in.

The main problem with autodownloading is securing the content.
The lua scripts could do nasty things, although since physfs was added we could presumably disable I/O from lua, although we'd also have to remove the ability to compile against system lua, which is currently allowed.
For now, we insist on review of all scripts that go on DLC.

Even w/ that problem addressed, there's still maps. To allow autodownload of maps, we'd need to have some review process in place to make sure people weren't putting porn, or worse, in maps.

One thing we could possibly do is allow autodownload of a particular script or map from DLC or Bender's repo.
We'd have to have some mechanism in place to identify the file name I suppose.

Also, we'd have to modify frontend at that point to intelligently reload, or you'd have to restart anyway, which is kind of a pain.
Limited reload for just things like maps and scripts is prob more feasible than the generic overriding of anything under Data.

But. It isn't terribly inconvenient to go to DLC, click on a link and restart, is it?
How often do you hit people using some particular script? Surely this is only necessary maybe once or twice a month?