Does the terrain restrict the population range? I saw a terrain I wanted but the village was too small so I hit Shift-Enter (repeatedly) ... and the population stayed too small.
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Is there a chance for the village to be located at the intersection of two or three main roads .. seems all the ones I see are plonked on an existing main road only. Intersections are important places.
Could you add generator options such as population and booleans for river and coast? That way I can quickly generate to meet a specific need (e.g. village of 320 pop, has a river, does not have a coast).
Additionally, they also tend to cluster around a significant resource - perhaps the big house of the founder, or a natural well, or (later) a church or other fortification. Perhaps take a melded approach - generate the minimal population founding settlement (by one set of rules), then expand on that with some organic (different) rules.
Looking at a few on google maps with satellite view, I see two common patterns: the ring wall with centrally isolated keep, and a ring wall with many buildings barnacled on the interior surrounding an open space.
The open space was usually used to marshall troops, or for huddled masses of refugees (e.g. all the rich bastards from city).
When it generates a map with a citadel, it is of a general size on the map (depending on small/medium/large) .. does the ruler scale make sense for that citadel, or is it suggesting that the citadel is massively huge or ridiculously tiny For example, according to Google Maps, Windsor Castle is about 450m end to end, Chepstow Castle is about 200m, and Dover Castle is about 100m (inner walls, or just 30m if measuring just the keep itself).
For small towns, the citadel building appears to be about 75m; medium towns have citadel castles of ~100m; and large towns have castles of about the same size. These are on the strangely large side.