A couple of weeks ago, I bought myself a Pogoplug (V2, gray) to try out. The PogoPlug comes with an embedded linux system, and is set up to externalize (through my.pogoplug.com) any USB storage device you connect to it. I wasn't as much interested in the services of my.pogoplug.com as I was in using the device as a general-purpose linux system.
Over the years, I've performed many upgrades to my systems. I've moved my desktop incrementally from Slackware 3 to Slackware 12.1, refining my process as I go. While the various documents and notes in each Slackware release do help, I've evolved my own upgrade "management reporting" process that gives a clear picture of what the upgrade will and will not do.