Workflow for 16G Usb key flash backup?

I put all my data on a 16G usb flash drive. It has something like 10,000 files on it, organized neatly in a directory with about 10 folders at the root. I use this regularly on both a PC and a Mac. About 8GB contains data. I want to back it up weekly, but how? Ideally I would back it up to another USB key on occasion as well as a hard disk.
* A file copy just takes too long and invariably stops in the middle with an arcane message.
* The external drive I use to back up the Mac is a Time Machine, which uses an incremental approach not suited to the USB key.
* I am willing to do something simpleminded, like copy the USB contents to a folder on the Mac, archive it, then let Time Machine back it up. That seems inelegant.
* I would be happy to delete the files on the duplicate USB key and recopy the primary to it. But...
* A related problem is that just deleting files on the duplicate USB key doesn't actually reclaim the disk space. Emptying trash does not seem to work either.
What's the best way to keep the USB key backed up?
Thanks!

This probably is not a job for software like Time Machine that is designed to back up whole machines.
You can try using regular old file sync software between any two drives. On the Mac such utilities include ChronoSync, FoldersSynchronizer, ExecutiveSync, File Synchronization,etc. You will find a wide selection of them at versiontracker.com or macupdate.com. Typically you can load any two locations into one of these programs and tell it to just sync 'em up. I use one to sync between a project folder on my Mac and the same project folder on a USB drive or another Mac over the network.
I guess you'll want to pick a utility that preserves both Mac and PC file formats.

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