I definitely had my framing dimension correct, but I think it was just the overhang dimension with the Gambrel style roof that was causing my siding to be cut off at the top. I ended up making some roof settings adjustments and adding shadow boards as my smart trim to the gables and eaves and that cleaned up the siding issue. Now the only thing that didn't look quite right was the eave but it'll just need to be depicted correctly on a section detail I guess. Thanks for the input!