Jeff,
Hopyfully we are there this time, with a possible solution (now that I have finally caught on to what you are trying to do!)
I could not get the TFP to slope both ways using the Pick Points method in one piece. Trying to set the inside edges to hip did not work. So...
In the example, I created the roof on its own Location, with the same settings as the ground floor - just to save any possible conflicts with walls etc. Then I drew each section of the roof separately (by Pick Points) simply butting up to each other. Obviously set the edges that meet to gable, before going on the the next section. I found it best to set the overhang to 1mm (fraction of inch) before I started, as the overhangs get in the way for editing later. You have to move the corner points close together (zoom in close). Turn off Object Snap or it will try to join the corner points and it will revert to the single slope or actually crash the program. SAVE, SAVE, SAVE as you do it!!! Reset the side overhangs later if you need them.
If you have any issues with the 5 sections of roof interacting with each other, then do it on 2 or even 3 locations, with opposits sides on one location and a single side on the third. May not need to do that, as I found it OK when Object Snap was off. Angle Snap should be off also.
I have attached the BLD file as well, so you can see what was done. It is a pretty rough Pentagon but served the purpose to see if it would work.
Hope this works for you.