I think sometimes we (I am an Ipad2 convert from a Motorola Xoom) make too much of Apple's "incredible length...to make file management difficult"

1. It's dead easy (even on unrooted Ipad to transfer files - just use Dropbox. Dropbox integrates nicely with many apps including IBooks, Stanza, Docs to Go,etc.)
2. Syncing with calendars like Google's or Outlook is equally easy - just use GWhizz from the app store (or any one of a number of similar apps)
3. Want to view a PDF - use GoodReader (which, BTW, is like a Swiss Army Knife for file transfer and also reads TXT files)
4. Want to watch video - Air Video is simple to use and free!
And if you wish to root (no chance of bricking the Ipad if you follow a few simple instructions) you can use IFile - IMHO an absolutely fabulous File Manager

So where's the beef?