I think that one of the big hurdles that people need to get over is to realize that the traditional way of dealing with files is not that intuitive, and has serious issues of its own. It's just that many of us are so used to it that we don't see it that way anymore.
I would encourage you to try a cloud app like Dropbox, Skydrive, or Box. These really simplify file access from ALL of your computing devices, not just an iPad. It's well worth the learning curve.
Oh I use dropbox right now and the apple cloud. It's fine for what it is but it's not quite the same thing as local file manipulation. It kind of works the same way.... But then it doesn't. It also requires an internet connection which isn't a big deal but it's still required. And, what if these cloud storage companies go out of business or get hacked badly? Just things to think about. There is something nice about local file storage that only you have real access to.