You make a lot of assumptions.
It's a game, anything is possible.
It may be a game, but it still follows some logic.
The Lore makes it pretty clear that Weirdwood is an extremly poor "village" (or rather gathering of houses) in the boonies with little to no interest in regards to infrastructure, resources or strategic value.
The people live simple lives and still have their issues.
There is no traderoute nearby and the village is mostly self sufficient.
Jenny barely cuts even and her husband gambles away the little she manages to save up... Rosy is faceing bankrupty along the miller.
Anyone else has barely enough to pay their taxes... aside of the mayor and Gwyneth I suspect.
MC builds several industries, like the farm, the wine and the Lustdrug deal, the temple and even get's involved with the Inn at the crossroads... he improves the situation of the people, but not the situation of the village.
He Upgrades most accomodations from shack to actual houses, yet he doesn't introduce trade, open mines or start a woodcutting operation in the woods... the only thing he further contribute is hunting Goblins and give their ears to Victoria to sell to some myth loveing nobles.