Override a class/add properties to a ListviewItem (vb.net)?

That is simply how it works. ListView can store any kind of ListItem and to get to the properties of your derived cast, you have to cast it. You are doing it correctly.

It's not a particularly good idea to subclass ListViewItem just to attach custom attributes to it. The class provides a Tag property for specifically this purpose and you should populate that with your own object instead of subclassing. It might not make a big difference syntax-wise, but it's a better design.

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