The problem is back in the nineties, when creativity ruled over profits in PC gaming, they created a lot of lore. Daggerfall was waaay too big a game for the tech of the time. They anticipated a market that would keep on growing and a franchise that would expand in a certain direction. They had no idea games would be limited by marketing constraints and cross-platform porting. They had no idea that future playstations would be so weak compared to PCs, but would still dominate the market. To create a managable, rich 3d gameworld a lot of stuff has had to be dropped.
You make a good point. Certainly in the case of the
size of cities which the in game books decribed, before they appeared in a TES game.
However, in the case of these smaller settlements or landmarks I see no reason why you wouldn't include them. Especially if they WERE previously mentioned in a book from a previous game. If I were designing the landscape of Skyim the first thing I'd have done is to go over, in detail, what had previously been alluded about Skyrim in in-game books and Lore, and build from there.