I'm using my 50GB box account, but sparingly. Currently, I have uploaded everything that was on my Dropbox, just to see how the upload process went. None of the files were over a few megabytes, so file size wasn't an issue. Next I'll try uploading my music folder (I don't have a whole lot of music in mp3 format, so it'll fit...) to see how that goes.
@4wd: Thanks for that, interesting methods. Not exactly what I was looking for, because I wanted to stay away from using other languages (no real reason, just personal preference). I'll post later with my current attempts using pure Bash, a combination of unison and rsync to keep files up-to-date, and Yad for the graphic interface.