Hi Sammidge, this isn't half bad actually, especially for a novice! I like the concept behind your map, and it look great too. One remark I'd like to make, even though it's far too late to correct that now, is the fact that rivers seldom flow the way yours does on the map. Rivers would only show this odd bump if topography forced them to flow like this. If it flowed over reasonably flat terrain and encountered a hill, it would flow around that hill with a far gentler curve. But don't worry, rivers seem to be one of the most difficult things to get right, both on regional and local maps. There's tons of articles on where to put then and how they work here on the CG, if you're interested.
- I don't think people actually built houses inside city walls. Any open space in a wall (such as a room) weakens the structure. But I know for a fact that in medieval cities many houses were buil against the walls (and churches, bridge pillars etc etc). Any vertical structure could be used (and was used) to support a house.
- Sure, that happened quite a lot. Not in the oldest walls, since those were usually erected with the shortest circumference possible (less wall to defend for the same amount of houses), but when a city started growing outside of its old walls, it happened that they constructed a second line of defence around the city, keeping some room for houses to come. The city of Cologne was one of those examples: check out this map for example.