Any reason why home sharing from a PC or Mac based itunes won't work for you? I and many people I know do this and are happy with it. I have my entire video library on itunes (media folder is on a SAN but thats irrelevant for this discussion) and through home sharing can access all the content when I'm at home over wi fi. I've never had an issue with it and works fine with my old ipad 1
pinkbellbird: guess theres no real way to access a flashdrive or external HDD with out using WiFi/Data?
If you are thinking about selling and upgrading seriously look at the android tablets. The ability to add a micro SD card and attach USB devices is very straightforward with most of the android tablets. IPads generally hold their value pretty well.