Bob has an iOmega portable hard drive that's starting to die and it's got all of his backups on it. He's trying to transfer the data, but his computer keeps losing the connection. Part of the problem could be that it's only drawing power from the USB port. It may not be getting enough power from the computer. So he should try a powered USB hub. He should also try another computer, like a desktop computer. If that works, then the laptop's power port, or the interface itself, is the issue. If the issue is replicated with a different computer, then it's the drive and he'll need to get the data off. He may need to bring it in to do that.
Another issue is that Windows had a terrible file copying utility, which is why they inserted a command line option called RoboCopy. But in Windows 8, that issue has been fixed.