Encrypted Backup From Windows To FTP/SFTP

Most of my background is the Linux/Mac world, but I do have ample Windows skill set, just not as refined or aware of all the available applications in Windows world, geared toward Joe User.

My accountant needs to run two sets of backups. First, he wants to backup his documents to an offsite location (space on his web hosting service) and he wants them to be encrypted on the web hosting server, which is understandable and recommended.

Short of installing TrueCrypt and using Filezilla with a manual process , is there any free or low-cost (but well supported) that would automatically upload revised documents and data files in encrypted form? This would not be very much data, just simple documents and accounting data files.

Secondly, he wants to have a "snapshot" of his HD to a USB portable drive (standard 2.5 HD). On Linux, I'd recommend Rsync, on Mac, Rsync or SuperDuper (and others), but on Windows, any recommendations? I see Unison, etc. I would just want it to update any files that have changed to make subsequent backups run much faster, such as only 15-18 minutes (depending on amount of data changed) and make the drive bootable, so in the event he looses his HD in his laptop, he could boot from the USB portable drive and be back up and running.

While I know I could easily figure out all this on a more manual basis, looking for things that would be friendly for Joe User to use and/or be something that can be setup and would run pretty much on it's own, assuming the backup drive was connected or system was on the Internet to upload the files, etc.