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In my opinion, this is a task that's like "shooting cockroaches with a tank."
I mean, making new dwellings appear on random maps is cool, but isn't it a bit too minor to justify messing with the executable file? As far as I understand, this process isn't simple.
In any case, I can offer some ideas on how to handle this without modifying the executable, if that helps.
In the game, there's a script command that defines which creatures can be recruited in a dwelling. There's also a command to "play an effect over an object." And there's a command to "change the name and text description of an object."
Therefore, you can create an empty dwelling without a model (or with a transparent model of some placeholder or sphere, so that it has a highlight). You can create several dwelling models in the form of effects. And you can configure a script that will change the creatures recruited in the dwelling and play different visuals by changing the effects. And you can also configure the description change.
By the way, this method can be used to create an upgradable or rebuildable dwelling.
I don't know how well the game script works with scripts. But, as an option, it might be possible to connect this script to the creation of random maps. If so, then this is how you can implement the generation of dwellings of different levels, or even dwellings of some neutral creatures.
But, in my opinion, it will require too much effort, and the idea isn't worth it.