Anyone trying to open the files, you will want to rename the statechart to Statechart 2.lvsc before opening the top level1.vi
Martym, what is happening is that the delay in your entry action happens within the run statechart node, which is before the outputs indicator in top level1.vi is updated. They are updated to have Calculating = TRUE, but then the statechart quickly takes its next step and leaves the calculating state and sets Calculating=FALSE, and this value flows to the indicator after this quick step.
I think for the behavior you are looking for, you would have the delay in an exit action of the calculating state or in the transition action for going from calculating to wait for input. Then you would take a step and enter calculating, Calculating would be set to TRUE, the value would flow out to the indicator in top level1.vi; then the next step of the statechart would have a 1 second delay before it could set Calculating = FALSE and this value could flow to the indicator in top level1.vi
Hope that helps.