If roof hip is on,Take off Estimate will not open.
If roof hip is off,Take off Estimate will open.With roof quants,minus roof hips
I've just tested this with my PlusSpec (Latest Version), and i was able to do a take-off.
I've got a few things for you to try.
First - Download the latest version of PlusSpec here:https://buy.plusspec.com/download
It appears that you may be using an Older version with a Roof Tool Bug.
Secondly - If this doesn't work try copying the roof into a new file and testing the Take-Off.
Give that a go, and post up how you go