yeah could be anything causing the issue, but trying a different computer will easily let the class know if its the device or the computer. google the error code and "android" with it and I bet you will see others with the same issue....
ive transferred video files without incident. i use the wireless way every time and it never fails. 1 gig total music is not a big deal. factors depend on your wifi strength, interference in the freq you are using (im on the uncrowded 5ghz freq and using a draft-AC router with a laptop that has a draft ac dongle).
give it a try. if these are albums then transfer one at a time or two at a time. if its just tracks not in albums, transfer 10 at a time, etc.
you know what they say, once you go wireless, you dont go back!