Drawing by hand is great fun, and all maps in the book can be done with pen and paper; each chapter will show you how to do the map with software. Digital tools will result in easier to edit and more readable maps while sacrificing the handmade charm. If you don't intend to sell your maps on Etsy or eBay, but use them as a communication tool, then digital might be the way to go.
I will use different software, my personal favorite for a map type. This, of course, doesn't mean that you need to use that software. This book is not intended to be a tutorial for any of those software products, so just use what's the easiest for you.
Always use the software you are the most familiar with for mapping. You want ...
