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If you don't want to do Version Control as others have suggested then I recommend Super Flexible File Synchronizer. It is a great product with lots of options in regards to what does and does not get sync'd. It is inexpensive to boot. http://www.superflexible.com/ftp.htm

Someone had suggested using Git and I was going to suggest the same. If you are only backing up documents then it should be easy enough to create repos on the USB HDD, Laptop and USB drive. You can then commit/merge changes between repos to keep in sync, perhaps use some shell scripts to ease administration. Also, I use a product called Super Flexible File Synchronizer to sync a subfolder on my laptop's filesystem with a WebDAV server. It's got lots of features and supports Linux, Windows and Mac. http://www.superflexible.com/

Try Super Flexible File Synchronizer http://www.superflexible.com/ I've been using it to backup and sync my files over SFTP and FTP to two different FTP sites. It can use zip file encryption on each individual file, and uses file name mangling to retain the date information in the file. All this is transparent to the user. It can run portably if you use Universal Extractor (a portable app) to extract the contents of the setup file, then after first run, in the Options, tell the program to use a single .ini file. This one tool does all that you need.

If something exists that meets ALL your needs, I've never seen it. Some of what you ask for is quite hard. We haven't found an exact solution but we have found one that meets "most" of your requirements. If you use Super Flexible File Synchronizer (SFFS) (http://www.superflexible.com/) and WebSafe (http://www.websafe.com/) you can accomplish the majority of what you want. SFFS provides a very flexible synchronization program that can be run manually or scheduled. WebSafe provides encrypted online storage for your files. File transfer is via https (SSL) with at-rest files encrypted using AES-256 encryption (in WebSafe). WebSafe provides both a browser and a WebDAV (Web Folder) interface for online file access. Binary diffs can be done for local synchronizations, but binary diffs would be extremely difficult to implement between a local binary file and a remote encrypted binary file. You sure don't want to have your files available on the Web in clear text (unencrypted). With the flexible scheduler available in SFFS and WebSafe's encrypted online storage, this meets our needs for syncrhonizations that exceed 45Gb of storage at our office.

I should let you know that as one of the programmers on the WebSafe team, we designed it to meet just the type of needs that you outline.

your backup has 2 problems. one is technical in nature, the second is operational.

1/ technical. you have lots of programs that can back up the data you need. and you dont have to spend a lot of money either.
http://www.superflexible.com/ lots of nice options, even copies locked files, dumps them to a drive, a tape, or ftp, just look at it. its not the only option, but you find people who have written software to do a job, not create a structure to rationalize screwing you out of thousands of dollars.

2/ getting your mobile staff to follow protocol and back up their laptops. now thats the hard part. you need to develop a policy on what do to make the backups work, offer some training if needed to get it right, and hold your contractors feet to the fire for breaking the policy. you clients data, your business data is the same as a doctor doing open heart surgery. "If you screw it up because you didnt follow a basic safety protocol, were going to pull your license"

There is no excuse for not backing up data. The tech to do it is cheap, getting staff to follow the rules is the hard part.

I've totally given up on optical media backups. The only thing worse than total hard drive failure is critical damage to a disc, where you know 99% of the data is fine, but the lookup table, or a key image segment is unrecoverable. I burn DVDs for organized offline storage and filing, essentially to free up drive space. If I'm REALLY archiving, it's two copies on gold MAM-A CD/DVD media, which Kodak is wisely OEM'ing now.

For 1:1 drive copies I have a 500GB external Lacie drive, which is big enough right now for two machines and a wee laptop. I use Super Flexible File Synchronizer to mirror. Expect to buy another Lacie at some point for shared working data / content creation. It needs decent ventilation; this summer the casing got hot enough to be painful.

I don't touch Maxtor drives anymore because my household replaced *FIVE* Maxtor PATA drives over two years. Warranty replacement drives would come back, and fail under warranty... I finally had to decide not to send them back to stop the cycle of pain.

Just sayin thanks 4 the info, webcalendar looks nice, downloading and playing w/ it this week...

rdiff - I'm lazy and use the quite nice, gui-full but shareware Super Flex File Sync. Works very well on the Win boxes I support.