How did you manage that?
TLDR -- Event structures are my favorite new feature. Try them out and see if you still hate LabView nearly as much. I also suggest not actually using any of your GUI variables. Treat these like declarations and use local variables everywhere else. Otherwise the wires are impossible to trace and buggy to change.
You've probably fixed it, but you can configure it to execute a code block when a value changes with Event structures.
This structure is a little new, but I started LabView before it existed so I only started using it in the last year or two.
It lets you define code to execute based on interrupt style events like "mouse release" on a button whereas in older versions I would wrap all my button checking logic inside of a big timed or while loop because otherwise as you've noted it won't update the value when doing the logic check.
So my old standard style would be that there's a timed loop around each case structure that is checking buttons at 1kHz against a local variable version of the button's boolean, with a sequence inside the case structure that always resets the button state to zero at the end. Otherwise it doesn't check for button presses if one has already been pressed and is running something, or if you have no while/timed loop it doesn't even check at all since it's a run-once program.
LabView patterns are really not very clear, and my least favorite bit is that there's at least ten ways to do anything, and only one or two are good but the others all logically seem like they should work until you look really close.
Edit: Or maybe my least favorite part is that despite being a system designed for instrumentation and controls and data acquisition, my god is it a pain to plot anything.