I am looking at your last circuit Robert
The way it sit, I read the following logic:
1- D6=Low, SW open
Q3=off, Q2=on, Q1=off
2- SW (momentary switch) is pressed now
Arduino is turned on, D6 is set high,
Q3=on, Q2=off, Q1=on, Q1 is latched, SW released, start timer
3- Time is up, SW is not pressed again, D6 is set Low
Everything is reset, Arduino is turned off.
4- Monitoring for SW press again
P.S.: I think I found the problem. When Q1 is latched on step 2, SW becomes redundant. How is the Arduino know if the SW is pressed and how is that effect the Arduino?
You need to find a way that even though Q1 is turned on and conducting, SW is able to trigger the Arduino!