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It would be nice with an expandable map where you could add the rooms and resources that players choose to upgrade, similar to the expanding castle in the board game Castles of Mad King Ludwig. Any ideas on how to do this for say Roll20? Any good softare where you can create rooms as separat maps and then add on to a map of the castle as the game goes on?

I used dungon draft to make the castle.
Easy to use and change. But its only beta yet.

I did exactly the same - Dungeondraft, but I think it is possible to make an upgrade on a base plan quite easily if you use layers (in VTTs) or cut outs (on a real table) and overlay the new rooms/buildings on the map.