@ng76 for populating a hex map I feel I'm getting great results with those old rules about Castles in OD&D, Vol III, page 15.
Place maybe 3-5 of those on a sheet of hexpaper and roll for what's there: you'll get cool inhabitants like a Lord with 1d6 griffon riding heroes or an Evil High Priest with 1d20 White Apes.
Some more rolls tell you their retainers, men at arms, number of villages and inhabitants they control, and how much taxes they get. Thus you get an idea about the economic outlook of the place.
When I put those villages around the castle within a radius of about 3 hexes, I draw roads in between and get an idea about the "civilized" parts of the land.
Potential conflicts start to suggest themselves. Maybe a first mission for the PCs?
Don't forget to roll up the treasure for each castle. After all these are "Lairs". Other Lairs can be rolled up and developed as they come up in wilderness encounters.
It's a bit like rolling up a subsector in Classic Traveller ;-)
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