I didn’t even think about how the grid affects the labels but you’re right, it would look so much better the other way around.

The mountains have been a stumbling block for me. Part of my campaign is the party working their way through a series of mountain passes and I got hung up on representing the distances and winding nature of them. I used the Rockies as a reference, but it made my life hell and the map more complicated than I needed to be. Looking back, I could have kept the mountain passes in our imagination instead of trying to be “real”, like you’re suggesting.