Current state of this piece:
WIP_HistoricalKane_v3.jpg

I made some labels way less curvy and I also started to do some variation on the mountains. So far, that variation is based on a collection of 7 differents brushes/stamps.

I give it to you Max, the straightned labels work better, and I actually like their current look (most aren't exactly straight, but kinda wobbly). As for the mountains, I am very unsure if the variation improves the piece or not... I think I'll invest on the mountain brushes a little more, just to keep experimenting, but... so far.. hmm.. meh...

@groovey: the mountains are more or less placed where I could spot them on the heightmap, but it doesn't really matter that much, since I am trying to recreate a map made by in late rennaissance - I actually think I should purposefuly make the map less accurate than it is right now. As for the rivers, I use the pen tool, and then "stroke path" with a 1px or 2px simple brush - wide rivers get a lot of wavy lines side-by-side. I'm copying this design from the original Russian Atlas I mentioned before.