Sync and Encrypt?

In search of a simple/easy tool to sync specific folders to my external 2.5" drive for offsite storage, I settled on "File Synchronization" (I have another drive that Time Machine uses).

(http://nemesys.dyndns.org/FileSynchronization_EN.html)

It's a simple program that easily does what I want - 1 way synchronization of selected folders when I tell it to. And the price is great at $15.

However - I wouldn't mind if my "Documents" folder was encrypted on this external drive just in case it falls into the wrong hands. Pictures/Music/Video don't matter.

I'm just wondering what would be the easiest / most pain free way to accomplish this? It would be great if the sync program could just do this for selected folders. Of course I could do it after each sync to the specific folder on the external drive, but that sounds like a drag.

Any ideas?

BTW - I was toying with going with an online service, like Crashplan - but in the end I like having the files on easily reachable media - I'll just take the 2.5" external to work and bring it home every couple weeks for a sync - or maybe I just wanted to buy another 1TB drive?

 

Okay - I've educated myself on encrypted disk images, and have thought about the best (i.e. easiest) way to accomplish what I desire.

Would it make more sense to create an encrypted disk image on my backup drive instead? I would then just sync my desired folders to the mounted image on my backup drive - unmount, and now all the data on the drive is encrypted?

 

Rethinking this further...I currently have 300GB with my video files - maybe that's overkill from an encryption standpoint?

Anyways, maybe I just encrypt on my backup drive my "Documents" folder? Put that into a disk image on the backup drive?

Ultimately I'm just trying to encrypt selected files on my backup drive for offsite storage, and not cause myself to "jump through hoops" on my everyday usage on my iMac. This way I only have to mount the encrypted drive on my backup when I want to sync...and then only for a small subset of the data being backed up.

thanks...