Unfortunately I have also not had good experience with the sync settings feature either. For one thing, I never understood when you click “sync settings” if you are uploading them to the cloud or downloading from. Either way, clicking it never did anything for me either in Ppro or AE. I don’t know weather or not you can retrieve your erased settings from the cloud, but I highly doubt it.
If you are on a mac, you can go to Documents>Adobe>Premiere Pro>8.0>Profile[username]> and there you will see a file called “Adobe Premiere Pro Prefs” and a folder called “Mac”. Copy those to your flashdrive and place in the same folder on the machine your moving to in order to copy the prefs, including window layouts and shortcuts. I don’t know what the path is for windows but I’m sure it’s similar, and a quick google search will find it.