I know my comment here is months past your posting and I hope you're still stopping by here at the Guild; but your Version 2 reminds me of some of the really old "portolan" and "regional" maps of early America. I have two old maps of the Cape Cod area of Massachusetts (probably remakes of originals for the tourist trade, but they are at least over 80 years old that I know of for certain) anyways, the only difference, to me, is scale and the addition of famous towns and houses and their famous inhabitants/histories. They also have stylized animals: bears, moose, deer, hawks, "mermaids", etc. along with a sailing ship or two. However, your map encompasses such a large "region" that this may prove intensely problematic.
I'd say, take what you've got, zoom into a specific area and detail the ba-jesus out of it with the ideas listed above, but keeping in mind to be having "fun" with it all throughout the process. I like the map very much. It has that real "antique" quality to it that makes it seem "collectible". Something a certain kender (in the Dragonlance Chronicles by Margaret Weiss and Tracy Hickman) would have "acquired" for his collection.
Good stuff, imho.