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There really isn't a reason, I don't believe, to use Flask over X. It's just as good, and it comes down to your needs.

To answer your first question: you use something like uWSGI. Flask, by default, stores sessions entirely client-side. You'll have to use something like Redis if you want to use more than one server (properly, anyway), but a Python app like this should easily be able to scale. It won't be Flask that stops you, anyway.

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