Another problem I've run into more than once is that many orgs don't allow ssh out through the firewall. One project I worked on recently the client had to send and receive data via his home computer after work and transport it to/from his work computer on a USB drive. Apparently that was fine.
Oh I am definitely not recommending this. It's just a warning of how people will work around any security protocols you put in place if they make it too cumbersome to actually get their job done. And in this case it was their secret data, not ours, so we didn't argue too much.