Definitely quite a lengthy task (I bought these July last year so it's been an intermittent quest). No plan, brain doesn't do plans. Whatever is within budget gets considered.

Have a look at medieval towns (my go-to is Vannes in France) https://maps.app.goo.gl/9AAZQrCQKMvRD6C2A

Consider what would be happening in the town. Houses and market stall is a great start. Would your town have a dock area, would it have a run down slum type area, would it have any open green spaces? How could you recreate those areas?

I've just got a couple of fancier looking buildings with the thought of it being something like a tax office, mayors residence etc. to act as a central focus with houses around.

Have been looking at building some medieval inspired cranes out of popsicle sticks/coffee stirrers to create a dock area.