@RedFennex Roofs can be very tricky to get right. I think I get what you are trying to do and from what I see, your build is pretty complicated when it comes to the roofs. Between the build having straight and angled sections, you're also trying to use curves in the roof. That is going to be really tough to pull off seamlessly.
That said, one thing I see in your pics is that you are using large roof segments. For a roof like what I think you're going after, you'd be better off using smaller segments. Get one segment the way you want it, then, move across the roof and do the next, etc. Think about using half roof sections in some places rather than the full section too. That way you get more flexibility with eave adjustments, curves and heights.
A complicated roof takes a lot of time to get right. And sometimes you simply can't get it perfect and have to settle for good enough. Only you can decide that though.
Hope this helps.