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Not silly questions at all! I’ll add a “how to use” section to the product since I made it kinda unclear on how to use if you’re not already super familiar with these. To answer your first question, each hex actually only has one feature potentially. You roll a 1d6, and you add a feature if you rolled a 1 or 2, or add a settlement if you rolled a 6. On a 3,4,5, you just don’t find anything, it’s plain ol terrain. As for the no repeats thing, that’s a rule to help make sure maps develop more naturally by limiting the same kind of settlements appearing next to each other. So for most settlements, reroll if you generate a tower or smth within 1 hex of an existing settlement of the same type, and for cities you reroll if there’s another city within 3 hexes. 

Here’s the intended flow: 

When you enter a new hex, you roll 1d12 to determine the terrain type first, that tells you whether it’s plains, swamps, etc.

Example: I enter a new hex and roll 1d12, and get 11, which is a Swamp. 

Then, you roll 1d6 to determine if there’s a feature on the terrain. In a roll of 1 or 2, you find a feature, and roll an d10 on the feature table to see what it is.  Example: I roll a 2, which gives me a feature.  I roll the d10 on the “swamp” features and get “hollow tree”. That’s just a cool natural feature in this area so I draw it on my map.

On a roll of 6 instead, i would have found a settlement of some sort instead of a natural feature, and roll on the settlement table to discover what it is.

Example: I roll on the settlement table and get “castle”. I check if there’s any other castles within 1 hexes. If there is, I reroll and use a different result, if there isnt then I can place it on the map. 

I can roll further on the settlement tables to determine the nature of the castle like culture, mood, politics, etc.