Hey, to be honest, we’re not really aware of any issues where properly set up devices would be going out of sync to each other.
It’s always a good idea to have the master clock signal sent out to devices through the DIN-5 MIDI connection, as it has solid predictability of timing compared to syncing via USB (including converting from USB to DIN-5 MIDI). So in your case, you could have Octatrack as the sync master, send out the clock to the rest of the devices, and make Ableton listen to the signal.