For my 10 cents you're over-thinking it before getting right into doing a map pick a small area and just go step by step:

1) pick an approximate style
2) draw mountains
3) draw rivers
4) draw cities and roads
5) draw country boundaries
6) add labels, cartouche, details

I think you'll learn more and faster when you put all the bits together right off. It will also force you to face some of the classical dilemmas of mapping sooner - how to make labels fit? How to show all that data in a 2D visualization?