Taking the hand-drawn route is the more difficult route unless you have some skillz and vision - if you have those then nothing else really matters except maybe some inspirations to prod you along or prod you away from. My advice is to look at as many maps as you can and save some so that you can inspect the techniques used. There are a few tuts for drawing maps (as opposed to generating maps with programs) for both software and pen/paper. So poke around and welcome.