Web to computer and computer to USB sync?

I'm searching for two programs; I want the first to synchronise certain files on the net (the latest msi's and updates for various anti virus and spyware tools, mainly) with my computer whenever they change, so checking every few hours would be fine.

The second tool I want to run when i put my USB stick in my computer to update it with these downloaded files.

At the moment I spend about half an hour in getright downloading these files and copying them across.

Obviously, the file names of some of these files change as they're updats (NAI's virus defs being one), and that's been a main stumbling point.

Anyone got any suggestions?