I just realized why syncing for iPhone/iPad is so painful. Apple wants to eliminate the idea of files and replace it with a more useful concept. I don't think they've finalized the concept yet, or exactly how it will work when accessing the same "things" for lack of a better word (ie. not "files") from multiple apps.
In the meantime they don't provide an easy way for users to sync files between iPad and your computer, not because there's no easy way to implement file sync -- Dropbox does a killer job of that across multiple systems-- but because they don't want users to bring the file concept from PCs over to iPhoneOS.
There's something else in store, and just like Cut&Paste and Multitasking when we see files replaced with "things" (or whatever they will be called) we'll understand why we had to wait.