1. Files as in ? You can only trasnfer apps,music,videos and the other few options iTunes has and that also only through iTunes.
If you want to go wireless,try dropbox or skydrive or google drive. They all have iOS apps in app store.
2. Same for photos, you can sync them via iTunes, or via any of the above mentioned cloud services-or you can use photostream. Am not sure about PC, but on a Mac, transferring photos via photostream is extremely easy via iPhoto or Aperture.
1. What type of files? And how tech savvy is your friend? There are a few ways to handle this.
2. For photos I use Portfolio. Don't have to use iTunes at all for it. But you do add a program on the computer that makes it the server for your pictures. What I like about Portfolio is you decide what photos others see. And easy to organize, and rename them on the iPad.