Also regarding the 8 sided roofs not properly aligning with 8 sided rooms those roofs are currently intended to have extended eaves or roof trims.
How to put roofs on octagonal room sims 4.
First place one roof as shown below and then use the copy room tool for that roof and place the other roof so that the roofs form a cross.
To change how much the roof bows.
Click on one of the spheres that are placed around the middle of the roof.
Now add two more roofs in the same manner as shown below.
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I hope this helps you even a little bit.
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It s pretty hard to explain but this is how i tend to go about roofing the houses i make.
Add a half hipped roof along one edge.
I will do a tutorial at a later point on how to make different types of octagonal roofs in the sims 4.
Click and drag the sphere up and down to alter the bow of the roof.
Best built on square or rectangular buildings start with a room on the roof level two or three squares in from the edge.
Repeat on all four edges.