@Max - I'l try it out, but it'l be tricky, since I never did it before. I tried regular labels on the mountains and it just looked really awful and started drawing too much attention from the terrain and actual mountains. I could take out the ocean labels and redo them, those would be quite simple, but the terrain ones will be tricky
This map is looking really nice, I'm going to have to give this tutorial a go one of these days. Thank you for posting your careful work, it's great to watch the progress.
If you're okay with the Pen tool in Photoshop then creating paths to type on is a snap, but you can find tutorials around for doing it. You draw a path and then hover over it with the type tool until the cursor changes. And then type!
PS. I noticed that the Eighth keep is missing the 'g'
I'm currently replacing all the names in this map with better ones (keeping some). Will have it done soon.