sday757

And to complete the answer I received to maybe help someone else in the future, it looks like to achieve the barreled roof that is a single click operation in the dormer tool, it requires some manual roof edits to achieve as a wall dormer. 

https://www.chiefarchitect.com/support/article/KB-00649/creating-a-curved-barrel-roof.html

https://www.chiefarchitect.com/videos/watch/746/drawing-curved-and-barrel-roofs.html

From a member, it appears you can create a "walled dormer" simply by creating a small room on the second floor with a ceiling height that punches that room above the roofline. Although I am still unable to put a barreled roof over that dormer without the barreled option as seen on the plan I'm working. (probably because a walled dormer like this isn't built with the dormer tool) 

stuck. I'm trying to achieve a dormer between floors as in the attached image. The second floor is 4' tall with trusses on top. I try to add the dormer on the 2nd floor and get ceilings too low. I can add them to the attic but it doesn't give what I'm looking for.  I painted the second floor brown to help illustrate. Thanks for any help.