We need to move. Forget side quests until after the main is finished. We'll start in one of the 4 areas, build it, go to the next, build that then once everything's built we can wrap it all together.
You're right, the hands of idleness close tight around our project. We should look for inspiration whenever motivation is scarce. I always find concept art inspiring, so I here's a vantage point of Newtown from the southern hills and a rough sketch of the leader/elder/instruction giver.
What's the first area and the goal to be achieved there?
The town. We need a complete, working town before anything else. A castle or tower should be under construction in the centre and traders should have stalls/shops around it. The player needs to be able to purchase equipment from the traders and talk to the leader/elder/instruction giver (who prompts a varying dialogue relative to the dungeon the player is currently exploring).
Once we accomplish those essentials we can celebrate the completion of our first area!
The second area and first dungeon is the forest on the eastern hillside (provided we're all in agreement to that part of the map layout).
*feels ignored*.....
Sorry Connors, those are nifty ideas.
I think we've finally settled on the Newtown story, but the destroyed town idea certainly sounds workable. You should discuss it in depth with Gnome, who has similar ideas.