Having GM'd sci-fi and near-future games for almost thirty years, I have finally decided to get into running medieval fantasy games. While I would still recommend picking up some references for medieval communities and history, this ingenious PC program is INDISPENSIBLE for doing several very important things:
This is the natural starter-point for developing a fantasy city, which you would then flesh out with all the references and cartography. This program even does some of the gridwork, for example with generating a market area. You can't beat it.
The very first feature you see is the city generator, which develops for you the character of the city you aim to build; what I mean here is what you say to the players. It provides you with what is called in literary criticism 'local color', and with the many (!) other tools provided (including a fascinating and highly entertaining tavern generator), you build the city up from there.
It's a superb tool whether you're just creating a bare-bones mental image of a city community for your players to flesh out in their minds, or as I suggest (and do), are building a full-fledged homebrew supplement but need a starting point to give you the creative juice-flow to begin such a daunting project.
EASILY WORTH THE PRICE.