Final Report:
Test flew before the club meeting tonight. All retract functions normal. Nobody, not me, anyone here, not even Robart considered the tailwheel retract air cylinder as a suspect. In retrospect, it should be considered just as any other air cylinder as they are all looped in together when pressurized.
Hope this helps someone in the future. I gained a lot of experience in the retract systems and hopefully it will be a lot easier to diagnose in the future.
Thanks to all who chimed in!