you should be able to tell the file in the disconnected drive, because it appears with an “unplugged” icon. And if you sort your files by modification date, the connected file will appear on top, and the disconnected file with appear in the bottom. So I don’t really understand the problem.
The true problem with your scenario seems to me that you have to tag each file twice. Right?
The good news for you is that we are going to handle synchronized drives (and folders) in Tabbles 3.1.
We also call this “Dropbox integration”.
With Tabbles 3.1, you will be able to tell Tabbles that a folder is synced, and therefore has a “twin” folder. This way, when you tag a file, the “twin” file will be tagged as well. You don’t need to tag twice.