So far in the WeirdLands I've gone and randomly placedlone- houses (1 in 6 chance), settlements (1 in 8), Towers (1 in 10), and Castles (1 in 12). Checked what was generated where, moved some about and added some where they made sense (some more villages near castles for example).
I have not figured out who or what lives where yet. I'm currently working on prettying up the map and making sure the terrain types match the descriptions tighter.
Here's two section of the map currently:
I'm not posting the whole thing currently as aside from having placed the icons for lonely-houses, towers, settlements, and castles so far I just haven't gotten to everything yet. Not sure about the icons yet, may have to scale them up a little.
Oh yeah, the samples here are in 150 dpi, the full scale version has them at 300.