Yes. You roll on the NPCs when you need any new ones (I suggest having one NPC for each Season 1 Day 1 Requests) In a group or with a GM, I'd say the player(s) do not need to follow the table and just make up an NPC if they want.
- The 1st, 2nd, 3rd means when you roll for the 3 Requests, the first Request rolled is that row of the table, the second Request rolled is that row of table etc.
- Heart Penalties is the penalty for not completing the Request before expired if you've taken the Request
- [times rolled] meant the times you've rolled that Community News specifically. Each building requires more materials basically.
I hope that answers your questions! Sorry I was trying to squeeze everything on one page and honestly some parts probably could've been more clarified.