Hi tshad,

Yes, I received the two files you sent me

The only way to design a roof for your floorplan is using the freehand roof, but first, you need to design the roof--> this is the most important step.
In the file you sent me, you outlined the floorplan with the freehand roof tool, so you got a roof with just one piece --> you must to draw / design each roof piece separately

You have several resources
1 - Power Tools --> Roof wizard--> you will get a roof composed by 6 pieces (in this case) so you can use it as starting point--> very important note--> you walls are mixed, so verify the walls in the perimeter--> they should be Exterior Walls
2 - In the detail tab--> you can draw the triangles in order to design your roof (set the ridge, sides, etc--> then select the triangles --> convert to--> freehand roof
3 - In the roofing tab--> design the roof pieces / set the elevations / set the pitch

Patricia