Hey there. I'm really glad you like the map! I'll see what I can do to help explain the steps I took to create it. This was a step along the road to a pseudo-isometric style and it was pretty long run to get this done as it was a new style.
First off, post a link to your WIP thread so I can see where you've got to. Other than that I can give you general tips. My workflow for a map like this is:
• Draw in the coastlines and get a selection that includes all the water (usually magic wand and then expand selection by 2). I use a 5px hard round brush with pressure sensitivity for the size for all my line work.
• Save the selection
• Draw in the rivers
• Line work on the mountains. First lay in the spiky top outline. Then go back and draw in the lines flowing down the sides. Make them a little jagged, and try to have one ridge line look like it connects to the next mountain in the chain to create a visual of a connected range of mountains
• Line work on hills and forests. Try not to be too careful with forests. They're an impression of burgeoning flora, not a load of individually drawn trees.
Next up is the colouring.
• Add a parchment background at the base
• Set up one set of layers for the sea, and another for the land - use the selection you saved to tell between them
I'm going to just talk about the land - the sea is mostly done with gradients and nice big brushes.
• Set up a colour layer and block in the colours of your land. Your parchment is brown so that's a good base. Take the tops of your mountains to grey. Tundra is a grey-blue. Plains are a yellow-green and forest a green -> blue green. Use a large fuzzy brush >100 px at least. This isn't precise stuff - you don't want hard edges on your colours.
• Add an overlay layer. Pick a dark blue for shadow and a bright white with a touch of yellow for a highlight. Use a hard round brush with opacity set to pressure sensitivity and lay in your mountain light and shade. This just takes practice, but what you want here is the sharpest contrast at the peak, fading out towards the base. Darken your forest. Switch to a grungy brush with pressure sensitivity for opacity, and low opacity (maybe 20%) and add some texture to the rest of the regions. Use a bright white-blue to brighten up the tundra, snow and desert.
• Add another overlay layer. Use a hard round with pressure sentivity for size, and perhaps an opacity of 50-80% and pick out details on your mountains. Use a grunge brush with scatter, colour jitter and low opacity to add texture to your forests. Lay some shadow round the edge of the forests to guve the illusion of some volume to them to stop them looking flat. Add texture to any area that feels it needs it.
That should get you 90% of the way there. I hope that covers a lot of the questions you had, but feel free to give me a shout if there's anything that doesn't make sense.
Oh, and the most important thing is that the line work pulls the colours together. The colours can (and should) be quite messy. But the hard edges of the lines give the colour structure. It's that interplay that gives the integrated hand drawn look and allows elements to flow into each other. Don't colour inside the lines.
Edit: I added some screenshots of the map with the various layers in order to show how the map was built up. I hope those are useful. Note all of these are at working resolution - so appear here 3x larger than they'd appear in the final printed product.
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