One of the best ways to move files to and from an iPad is Dropbox. I have been using Dropbox free account now for over nine months and it has been great. Last fall my HP laptop died when the power on button snapped off in my hand while traveling back from a speaking engagement in NC. I am so grateful that my partner, Tommy Stephens, had recommended Dropbox to me a few months earlier. As soon as I was able to get a new laptop I was able to quickly restore all my critical teaching data and some very important personal files. No, I don't put anything up in Dropbox that contains sensitive personal information but i probably could as Dropbox is both encrypted in transit and encrypted at rest. If you decide to use Dropbox for sensitive data be sure to evaluate the security policies before you put up sensitive data.
Right now I had Dropbox on two Windows-based PCs, one Macbook Air, an iPhone, iPad, and iPod. All my data flows accross these devices seemlessly. I haven't been this excited about a sync tool since Windows 95's Briefcase.
Here is a referral link for Dropbox: http://db.tt/Cl16SlXj
Next week I will write about SugarSync.