Quick update,
a bit of google-fu took me to the following page:
http://forum.allaboutcircuits.com/threads/auto-off-switch.27626/
I think I have found a neat solution to my power on/off switch:
My version will have the line that goes to VDD connected to the 3.3v converter ENABLE , that will in turn power the Trinket Pro, which will then pull high the BS108G gate to keep everything powered or pull it down for auto shut-off, while monitoring the line currently connected to pin 4 of the picaxe in the schematic to monitor for a turn-off signal.
SWEET!
Cheers,
Mick
EDIT: Both transistors are reaching End-of-life and are not available anymore for purchase... let's look for alternative transistors.
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