Reading this blog series against the backdrop of background conversations with Indy Johar, and contextualized with our own bioregional work at r3.0 (in the Connecticut River Valley bioregion in the US), I must say that I am deeply impressed by this series, and also appreciate your humility in your postscript, Emily.
In response to one of your questions ("What are we pegging a system’s health against? How can we estimate what the optimal regenerative potential might be?"), I would strongly recommend using ecological and social carrying capacity thresholds (some have become familiar with these concepts via the Doughnut (2012) and Planetary Boundaries (2009) or Context-Based Sustainability (2008) or even earlier via the Ecological Footprint (1993) or the UN Cocoyoc Declaration (1974) or Limits to Growth (1972)) as the baseline against which to assess bioregional health.
Our bioregional collaborative spec'ed out such an approach a couple of years ago (with partnership with Regen Network, Prosocial World, etc_ in a grant application to the National Science Foundation in the US, but we didn't get the grant, so we weren't able to pursue it further, but that conceptual infrastructure remains available to pursue further.
Since then, a set of thresholds-based indicators -- the Sustainable Development Performance Indicators -- have been released by the United Nations (that we supported them to develop) as a maturation of the Sustainable Development Goal indicators (which lack sustainability thresholds).
I would welcome conversation on this, if you wish.