Ok I finally have time to respond.
I can't put into words how amazing it is that you made this beautiful map @Vainamoinen. I love maps! My brain always tries to draw one mentally, and Mêlée Town specifically feels so real to me.
This tiny move to the left Guybrush does while approaching High Street now has more context. I can see him going down that route you drew, followed by him climbing some stairs.
Also, wild: I never felt that the town is built on a hill that you are climbing. But it's so obvious: Where is the water next to the mansion? I never really questioned it.
Anyway, just some random thoughts that your map gives me. Amazing artwork!
(Also: "Gefischtwarenladen" )
Duke Nukem voice: "Ooooh! A circus. I love a circus!"
This looks so good. Back then I made a ton of levels in the Build engine. I love the restrictions of those old engines, they have this unique aesthetic.