SpiderOak <--

It's like dropbox except that it's encrypted locally before transmission to their servers so the company only sees ciphertext.

I'd skip all the steps about truecrypt and just use spideroak.  If you want to use the email backup method, then 1) schedule jobs to make backups, 2) use whatever encryption capable archiving tool you like, such as bzip2+openssl or in windows 7zip/WinZip etc 3) use a command line emailer mail/sendmail/sendEmail/etc in linux or something like blat in windows, to automatically mail it to your gmail account.