Decide how much each roadmap item leans on agents

You are planning a quarter for a 6-person team. The roadmap has 5 pieces of work:

1. a new internal analytics dashboard
2. moving a 12-year-old billing state machine to a new schema
3. generating 200 CRUD endpoints from an existing OpenAPI spec
4. a new scheme for merging offline edits from the mobile app, with no reference design to follow
5. routine dependency upgrades across 30 services

How much should agents do on each item: most of the work, close assistance or little? Decide each one, then state the principle behind the split.