re: #1 I have a skill that essentially manages a daily board in json format and pulls in active or potential tasks from all my work streams (email, slack, grafana, ado, or even manual input). I have this management plane keep a journal for each day and then spin off sub-sessions to work individual items. I pretty much just run the thing on a loop, and since context is stored with the board itself there’s no issue closing down and restarting the session or clearing context occasionally.