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I run the SQLIte3 utility from time to time. Do I really get any benefit out of it? If I do, can you automate or "user" schedule it to run? I suppose I could script a Windows Task, but is it even worth the effort?

I don't actually know what you're doing so, I don't have an answer. I never do anything to my databases. In the right click menu/post storage, there's an option to compress the database.