Not intending for this title to be click bait, but I contacted Elektron and they had some helpful tips (for this noob anyway) and I thought it might help some others. This is the gist of their suggestions:
Make sure that you have installed OS 1.30B on the Digitakt. We fixed a bug that is related to Overbridge sync for this OS.
Note that you don’t need to sync the Digitakt via MIDI while using Overbridge, as sync is handled via the plugin. It can even cause problems to also sync via MIDI at the same time as syncing via Overbridge. You can disable CLOCK RECEIVE and TRANSPORT RECEIVE in SETTINGS > MIDI CONFIG > SYNC in other words, if CLOCK + TRANSPORT is enabled in the AU plugin.
Additionally, you should set an appropriate PLUGIN BUFFER SIZE in the Overbridge Control Panel settings (click on the small cogwheel symbol in the upper right corner of the Control Panel to get to the settings). I would recommend a buffer size higher than 128. The buffer size for the sound card functionality is set separately in the host (your DAW or the standalone plugin).