doublepost! you posted an update while I was typing my last one out Awesome work, it's looking more natural.

Another thought occured to me, in an earlier version of the map, you had your writing kind of all over the place, and then you tightened it up so it's all straight lines. I'm guessing you were going for the "this all got handwritten out by someone in a hurry so they didn't have the time to write in nice neat paragraphs"..

I've got a rather time consuming method that works wonderfully - I've used it on a few maps (mostly the Gromet and Friends maps for the Passage of Time and Trade challenges).

Once I had all my text placed out the way I wanted it, I went nuts with the pen tool, drawing out a separate line for each line of text that was being placed. I then tweaked each of the lines so they had a few small bends, changes to angles, and in some cases even picked out a few bits where I widened the text or shrunk it ever so slightly. That gave it a more organic feel, but if you do that be careful, people typically have a tendency to write in relatively neat lines but a few subtle variations can make it look very natural and handwritten.

Of course the ultimate way of doing that is to actually write the text out yourself on a piece of paper, scan it, and add as a layer overtop set to multiply
If you do that, run your text layers out on a printer, that makes an excellent guide for writing by hand, then run it through the masking process above.

This all assumes you have a scanner, printer, and the time to do it (or a bit of affinity with the pen tool, and lots more time)