I've figured it out! The problem is with the extension that has your library precached to send to your device and it might include references to files that no longer exist. To fix this simply remove the extension, install it again, add folders to your library and pair your device.

Reinstalled Chrome for another reason, tryied again and this time it worked perfectly. Consider this issue closed.

I can't seem to pair with my computer, the app tells me to now go to my computer to finish but there's nothing there. What am I missing?