@scott , I appreciate your initiative, effort and good will.
However, the main problem that many of us have with Wordpress.org chiefly concerns governance (as embodied by Matt’s one-person legal control) and its impact on technology/deployment choices and timeline, rather than the technology itself.
Complete legal control held by one person is too risky for many reasons. Polls and talk about democracy are great, but then Wordpress.org used to be a lot more inclusive as well. Yet all that is at the whim of the moment for whoever legally controls an organisation, whether it be Matt, yourself, or another person.
While it is important to take the time to find the best additional directors, I urge you to make this a high priority. Building up the community’s confidence in the governance of Classic Press will be a key in the decision of power and enterprise sites to convert.
Further, Wordpress.org is not the only competition out there. It is not that difficult for power users to knock something out in Ruby on Rails, etc., that meets their needs and that can even use the TinyMCE editor. Yes, they would be giving up the ecosystem of WP plugins and themes, but that whole ecosystem is getting really disrupted (and possibly diminished) due to the Four Phases of Gutenberg anyway. Please help make the decision to convert to Classic Press easier by reducing governance risk.