It is from the previously posted map tutorial KS project that I found another that (thankfully) reached its goal in June 2012. Cityographer mapping software.
This can also be found at http://cityographer.com/ and http://inkwellideas.com/.
Simple and compatible whether you're a Mac man or a PCer, like myself. The video makes it appear ridiculously easy to create highly detailed, editable cities and towns, right down to the name of the blacksmith and what items he has for sale.
He makes mention at 9:52 in the video of a medieval demographic calculator. These are the two that I always use Medieval Demographics Calculator and Medieval Demographics Made Easy.
At sale prices of around $26 each - because Hexographer and Dungeonographer are also available - and add ons for about $20, it all adds up to a well-spent $50.
Once I've saved my pennies and gone through the couch cushions a few times I'll purchase the pack myself and begin sharing/posting the maps I've created. Stay tuned.