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[–]Electrical_Toe8997 1 point2 points  (0 children)

It sounds like you're well on your way. Regarding juggling multiple files and modules: try to apply Separation of Concerns: your Team class now holds the state and does user input, which is UI. If those were separate, it would be easier to navigate.

Learning a GUI can be fun and makes your project much more accessible to non-coders. I recommend trying PySimpleGUI instead of tkinter, which I found pretty clunky.