I spent some of the past weekend playing around a bit more with Hexographer in order to finish off the last few sections of the initial starting area for the Dwimmermount campaign. The area is (obviously) based on the Outdoor Survival map, with some tweaks here and there. It represents most of the ideas I had when I started the campaign, though, in all honesty, very little of what you see on the map are more than names.
Throughout the course of the campaign (still sadly on hiatus owing to scheduling issues), the PCs didn't venture farther into the world than south of Yethlyreom (labeled "Temple of the Moon" on the map) or farther north than the southernmost edge of the Evensong Woods. Most of the action in the game took place in either Dwimmermount proper, nearby Muntburg, or Adamas, with a few visits to Yethlyreom. So, the farther you get from those areas, the less detail you're likely to see on the map.
Lest there be any misunderstanding, I don't think there's anything wrong with alternate approaches to world design; they're simply not for me. Of all the lessons I've learned since coming back to old school gaming, it's keeping the focus on actual play that has had the greatest impact on me. If I'm not likely to need something for the next session or two, I generally don't bother with it. Plus, I get a thrill out of seeing what pours of my subconscious when I have to invent something right then and there in order to keep playing. It's not to everyone's taste, but I love it.