you can do hand drawn digital maps. It's all a question of the equipment and hardware you have. There are a range of tablets that Wacom makes you can get. They even have the Cintiq line of monitor tablets. That's what I use, the Cintiq 22HD touch.

Either tablet or monitor, you have a stylus with which you draw with. All my maps are made via a combination of digital and scanned elements. But in the end, I draw every mountain, hill, river and letter. Does it matter if you are using a crayon, pencil, brush or stylus? I seldom use filters, because they tend to leave a signature that eventually you can spot. At most, I use color correcting more than filters.

And there's a range of software too. Painter is my preferred program. But it takes a lot of experimenting to start to understand it. I don't recommend it for the casual person. Get photoshop and find some good brushes.

There are lots of advantages to working in what I call a digital traditional method. The main one being able to correct, or adjust as you go along. Being able to test things out, without having to start over or figure out how to correct it. Doing hand lettering is much easier, as you can lay the text out and then draw/write over that, then delete the layer below.

it all comes down to what you want to do and how much you can afford. My monitor cost $2500. But I'm a professional illustrator, that works digitally, so it's for my work. I wouldn't suggest it for the casual user.

And yes, post a bigger, nicer shot of that map you are working on. It looks very interesting.