A lot of the questions that you've been asking are easily found in the object browser.. you should take a look. There's a search feature to boot, just do a search for ListBox.
Look up controls in the object browser, trust me it will answer a lot of questions on how controls work in .NET and answer a lot of your common questions.
You have to get used to the fact that in Vb net a list now contains objects.
I am not sure if I am correct in doing this but I have the tendency to create my own objects, overwrite their toString function and add them to the list. I always cast coming out also.
Very similar to Java if my memory serves me correctly
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