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When I click the Go button, I want the status label to immediately display the text "Working...", then I want to carry out some time-intensive tasks.
Any change in the GUI from the new thread needs to be done in the event thread (or main thread) (you can use invoke Later()).
It may be repaint(), as someone previously pointed out, but I'm not too sure on that.
I don't have much experience with the AWT or SWING toolkits, but I imagine something like this should work. Rather than looping through every button and checking to see if they need updated, you can probably just directly update the two buttons that need updating.
You should have implemented your terminal prints before you even start coding and i don't see a single "println".
Adding the JButtons with a forloop is fine i don't see an issue.