What size hard drive are you using? If I remember correctly (haven't messed with this in a while) 320 GB hard drives don't work. If you're not using the 320 GB, I do remember the program would give me trouble sometimes, just unplug and plug back in going transfer cable first then hard drive into the transfer cable.
As far as the drag and drop, is that not working? It should work, if it displays a circle with a slash through it (I think that's what it was) then you're User Account Controls are set to point where the program won't let you add the file. The solution to this is to search for 'user account control settings' it should open an application and the bar should be set to default, go ahead and slide it all the way down to never notify and restart your PC and then you should be able to drag&drop. Obviously this exposes a risk to your computer and it is not recommended to do this so after you're are done with the transfer I recommend changing it back to default and restart your computer again to save changes. If it is too much of a hassle and you're loading rosters constantly you can leave it at never notify, but beware your computer will be at risk and I would only do this if you know what programs you install and what they are able to do.