No difficulty at all with synching it. It took a good bit of time to physically copy all the files over, but there was no fiddling. You just plug in, register the device, and tell it to synch. Then you can go about your business while the files transfer.

After that I reset it to manual update so I can drag things around between different computers.

It was much less hassle than it has been ripping the HP audiobooks, frankly, because GraceNote has inconsistent titles and listings for each disk and then I have to batch them all to the proper settings and structure the naming of the albums so they sequence properly. I feel like it's not too much work since I am getting them free from a friend, but it would be exactly the same work if I had paid for the disks, and then it would annoy me.