I know I (and others) have mentioned this before but Dropbox is one of those things that just works and is brilliant for anyone managing more than one school.
You just install on it on your servers (and home machine) and any files put in the dropbox folder are autosynced across all machines.
No looking in pockets for pendrives - no losing pendrives!
If you haven't tried it - do it :-)
If your LEA block it - lean on them!
Get yourself one for Christmas :)