Button states and confusion

I do not understand what you are trying to do. But, it sounds like you want a state machine. Start by drawing a state chart. The state names go in circles. Transitions are arrows from one state to another. Along the arrow, put the event that triggers the transition.

You may have more than one event that triggers a transition, from one state two more than one other state. That is fine. The same event (the START switch became pressed) can trigger more than one transition.

Show the diagram, if you get stuck drawing it, or implementing the transitions.