Awesome. I'm using an OS X desktop, by the way, but could use Windows if I have to.

I just managed to use the commandline to sync from a folder on my desktop to my tablet over ssh!. I used this string, found elsewhere:
rsync -avz -e ssh remoteuser@remotehost:/remote/dir /this/dir/

This should work just fine, as long as I can get the password to be automated. I know there's a way to share a key between the two machines, but is there a way to add my password to the string?

Edit: I also want to apologize. It looks like I asked almost this exact question early in the year. I certainly feel like a chump for asking again, and not finding that thread in my searches. I promise I searched (both google and site search) before asking again. It looks like an answer might come out of this, so at least it was worth bringing up again.