I did some more experimenting and here is another way to do it, if you want to use Ableton as Sequencer to the Digitakt/Digitone and still want to use Overbridge to split the Audio channels.
You still limited to one instance of the Digitakt/Digitone VST, as like I said, the sole purpose of the VST is to split the audio tracks. That’s it.
But at least for those interested. Here is an example screenshot of my experiment, to send individual Ableton sequences to in this case Track 1 and 2 on the Digitakt and then Output them over separate channels back into Ableton via Overbridge(Digitakt VST):