Well I had a few hours this afternoon so I already knocked up a rough test map to see if I could do something in a similar style to the first image you posted.

This is what I came up with so far...

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But that new image you posted changes the game somewhat as the first image is nothing like the second one so that's kinda mixed signals right there.
I presume you have trawled through the completed maps and searched for a map in a similar style to what you are looking for?

My own usual style is for a hand-drawn type map but unfortunately nothing like Torstan's that you posted. Here is my latest WIP just in case...

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