I think "wouldn't it be cool if..." is a totally valid way to approach creating a map.

One thing to think about is who, in your world, is drawing this map, and how much do they know about the places they're mapping? A lot of things that might seem geomorphologically implausible if we assume high accuracy can make sense as a stylized way of representing something the mapmaker doesn't know much about. For example, the roundish blob of mountains in the southwest isn't something we see on the real earth -- mountains are usually in linear ranges -- but if all the mapmaker knew was that this land had mountains in the middle of it, that's a fair way to draw it. If this is for an RPG you can even work that into the campaign -- some areas may get "clarified" once the PCs actually go there.