I do have two dongles, yes. One is for my home pc, and the other for the work pc. The home dongle has the 8.5 license and the work dongle has the trial license.
When I tried to access the VST Transit feature I unplugged the work dongle and plugged in my home dongle before firing up Cubase. The feature was still not accessible.
So for example, now I only have one dongle plugged in. It has a full Cubase 8.5 license on it (which I have confirmed in the eLicenser control panel). I then open Cubase 8.5 and create an empty project. Under the VST Cloud drop down only VST Connect shows.