The v_in was stuck at about 2.4V drawing about 56mA never reaching a higher voltage in order to activate the 3.3v regulator. In order to see more energy and perhaps climb over this 2.4V I added another 100nF capacitor in parallel. In total this is 670nF (470nF + 100 nF + 100nF) which is a 43% increase in energy storage capacitance!
Start up the oscilloscope, and plug in the KAW! It's not the smoothest but after a few seconds, the circuit does achieve its goal to power the moteino microprocessor!
1) 0.0 to 12.5 (12.5 seconds) output is about 2.3 V. The KAW screen is completely dark during this time not displaying anything.
2) 12.5 to 21.3 (8.8 seconds) output is about 3.3 V. You can see the 13V9 line start to increase, and this is not causing a proportional climb in the v_in. The KAW screen is now showing the correct voltage on screen.
3) After 22 seconds the output finally reaches about 5V for steady operation on both the KAW and the moteino.