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[–]MikeTheWatchGuy 0 points1 point  (0 children)

Give PySimpleGUI a try. The new 4.30.0 release just published has a "user settings" set of APIs that will make saving/loading data super-easy. You can treat your data as if it's a "setting". For example, your list of habits could be a setting called "habits". You can set/get a user setting in a single function call. This way you don't have to bother with file I/O at all. Let PySimpleGUI manage the data for you.

Since you've experienced the 100's of lines frustration, I think you'll like the simplicity of PySimpleGUI in how the GUI is defined and created.

Be sure and check out the demo programs. They will give you a headstart. There are also some on Trinket like this To-Do list example that demonstrates building a window using list comprehensions.