Thank you folks for this awesome update! 
The level of detail and depth of the questions is truly impressive and puts us on a great track to figuring out what our next steps in the transition need to be. 
A few thoughts below:
Maybe we can workshop this with the whole team at the next offsite? I know team autonomy is very important to the core teams at Radicle, but this seems like a pretty big issue that should be addressed for long-term sustainability and overall well-being/sanity.
Having this list of specific subjects folks are concerned about is super helpful. There seems to be a desire from the Radicle community to have a better distribution of influence amongst the core team - especially for decisions relating to the treasury. I don’t know how helpful or dangerous this would be, but maybe it would it make sense to lightly start defining/sorting out what types of decisions could be made by a level of “core team governance” (for example working group budgets) and what should remain in the hands of the wider community? I say “dangerous” above because we don’t want the community to feel that they are being left out of important decisions. But taking an example from MakerDAO, it has been extremely stressful for teams to have to rely on the community/wider governance process to approve quarterly budgets for each team. It makes planning really difficult.
Clear, easy to find documentation, consistent on-boarding process for ALL members (new and old), simple and efficient tools members can plugin and out of as needed (especially for governance). There are of course a lot of other important pieces here (including a lot of admin/HR needs) but I feel these basics are important to nail.
We could set up some sort of tiered onboarding flow. Folks who are hired could receive a NFT badge and with that access a new tier of information/onboarding docs in the flow. I know DAOLens has this capability in their onboarding flow for example.
I am currently trying to do a more detailed mapping of our tooling needs and what is potentially available to us. I want to have this and next steps up by the end of this week or early next week!
One questions I did not see here (maybe in a different post but I missed it?) is regarding liability. For example, if Radicle gets in trouble with regulators or is sued, who acts as the entity responsible for representing the DAO? I have heard some horror stories of legal entities going after the core or founding team of decentralized entities who have ran into trouble in the past. How can we ensure core contributors are protected and what is the plan of action if something were to happen?
Thank you again for the TLC you folks are pouring into this. I look forward to continuing the discussion!