yes, the phone works, he is just tired of not being able to sync to computer. Not in dfu or turned off, it is on when plugged in and message prompts. He is considering upgrading to 4.1 or something to get it to work, but there is an app that he would lose that is no longer 'fully' available
Not sure what your problem is but you can update itunes to the latest first.
If you don't need unlock , then download 4.3.2 firmware from google search iclarified firmware.
Run itunes : shift + restore to 4.3.2 and jailbreak it with Redsn0w RC14