Have you tried without using Overbridge? If all you want to do is triggering seperate midi tracks to the Digitone.
Overbridge is only needed if you want to record the four audio tracks to seperate channels.
If you want to trigger 4 separate sequences from Ableton to the Digitone, you need to create 4 midi channels and one audio channel.
then configure it like I show on the picture below I did for the Digitakt as example:
Then the Audio track needs to be set to Ext In and then select the Audio Input channels from your interface to what the Digitone is connected to. Like Line 1/2 or 3/4, etc.
Then set Monitor of the Audio channel to In to arm it and be able to hear the audio from Digitone coming in.
Hope this helps.
PS. If you want to do it the other way around and sequence 4 different VST’s in Ableton via their own Midi channel and use the Digitone as a Four track sequencer. Then it’s the other way around and make sure you arm each channel by setting Monitor to In. Otherwise you won’t hear anything!:
I run the latest Windows 10 patch level, latest Ableton Live 10 version and have no issues sequencing seperate tracks/channels!
But you have to do it and configure it like I described above or it won’t work and/or won’t hear anything.
I regularly use the Digitakt to sequence VST’s and external gear through Ableton Live (even without Overbridge) like my Behringer Crave and Novation Circuit, but it’s important to setup both the Midi and Audio tracks correctly!
In this example, Novation Circuit’s two synth tracks only listen on Midi channel 1 and 2, so I set the Midi channel dip switches of the Behringer Crave to listen on Midi channel 3. Then VST’s l configure to Midi channel 4 and so on.
Also, like above mentioned. Go to settings in your Digitone > Midi Config > Channels > Here make sure each track is listening to the correct Midi Channel they are supposed to receive Midi data from (when sequencing to Digitone from Ableton) or sent Midi Data On (when sequencing from Digitone to Ableton) !