I found some stuff on Google today...just had to figure out how to word my search!... Here's what I camp up with.
cat /localdirectory/file.mp3 |ssh username:email@example.com "cd /remotedirectory; cat > file.mp3"
That works...except it asks me for a password (which needs to be fixed if this is run as a cron) and I can't seem to specify the whole directory...just individual files (which will change names on a weekly basis).
Why the cron doesn't work on the mac? I don't know for sure other than to say, it's a M-A-C!