Hello,
I am a happy consumer of maps and have been for many years (mostly for gaming purposes). But lately I've wanted to up my game and actually overcome some of my technical limitations and do up my own maps. I nerd deeply about languages and cultures and history, ancient and semi-modern.

My near-term goals are not to draw my own freehand maps. I could do that, but what I really want to figure out is a good way to take existing historical maps and modify them to where they have all the things that I want on them, instead of using someone or somewiki else's maps with 30%-70% of what I want depicted.
I would happily take guidance from folks on user friendly software and so on.