Hi Cameron,
> Currently, the widgets do not update until we make an extra click to the select tool. Is there a way to have the select tool on by default with the map ...
Your first statement describes the expected behavior in Operations Dashboard at this time. For your second statement, please vote for this enhancement request on the ArcGIS Ideas site; this will help us prioritize the enhancement request.
https://community.esri.com/ideas/15496
Hope this helps,