I think there's two issues at work with your comment mikie. The first, which many historians have spoken about, is that the lost habits of letter and diary writing mean that much less material will be available for historical analysis in the future. Email archives aren't as common as boxes stuffed with old letters, and email archives typically have much more worthless stuff in them. The second thing, the changes in storage media over time, I think isn't so much of a problem. There used to be lots of stuff stored on 8 and 5.25 inch floppy disks. They're not lost to the future, that worth keeping was migrated to later generations of storage media. Places like the Library of Congress and National Archives are digitizing many parts of their collections to protect the availability of their contents for the future. All that stuff gets rolled forward as technology changes.

Create the PDF...save it to your local machine...drag/drop it to the flash drive...what could be simpler? Am I missing something?

I buy the flash drive wallets which have slots for each one in it, I have bought them at walmart for around $4-5 each and they hold several. You can put a label in the slot with the flash drive or if you have a label maker you can put a label or code right on the flash drive. If you use a code system then just put the list of codes in the storage wallet with those coded ones. You can also store a document on each flash drive that lists it's contents so that you just insert the flash drive then go to that document file to view what you stored on it. Case Logic USB Flash Drive Case for 6 Drives, Blue you can just google flash drive cases for other options

Yes, a flash drive is essentially just like any other drive, and as pkponder says, just use Windows Explorer to drag folders and files into and out of it. Make sure your different groups of files - say photos - stay in their own Photos folder on the Flash drive, so things don't get all mixed up. Make new folders when necessary. When you get to the new computer, just drag files to the places that you want them - probably similar locations as in the old computer. Also I always use a two pane Windows Explorer view so I see the folders on the left, and folders and files on the right. Open up as many Windows Explorer windows as you like, and drag from one to the other. You can even do copy and paste. Try experimenting a little bit - you'll probably find it's not that difficult. By the way, Microsoft has an Easy Transfer Tool which started with XP but I believe is builtin starting with Vista. That would probably do it all for you : http://www.nextofwindows.com/how-to-using-easy-transfer-to-migrate-data-between-xp-vista-windows-7/ and the following . . . It looks like you have to start with XP, but I believe it works just as well starting with Vista. Here is a link that might be useful: Migrate XP to Windows 7 with Easy Transfer and a USB Drive