Do you have any ideas on how to transition from outdoors to indoors? Think it'll be possible to stay on the same part of the map and remove the exterior when the player enters like some games do? Or should the player be transported to the interior implemented elsewhere?
The shadows are part of the same tiles, yes.
The tiles are much larger in this case, yes. Some are twice as large in both directions. Some are twice as wide and three times as tall. Building in pieces is still necessary so you can get houses connected in different ways (rather than just rectangles) as seen in the image, but the whole bottom is in three pieces, Left, Center, and Right, as is the middle and top.
I have since moved different groups of images to their own tilesets, so it's not possible to have this on the same layer as trees and rocks, or on the same layer as fences (on their own layer). This is one of the reasons I wanted the ability to use solidity information from several different layers all at once.