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Have you looked at something like the Laravel framework for this milestone? I know it'll be a beastly migration from the current setup but I feel like it'd be such a flexible fit for the future, it has built-in database migrations and such and a way to have your own account system without WordPress.
I never worked with frameworks so far, I don't know how much of a change this would be. It's likely a good suggestion if we start working on this topic more seriously.
To make the server portable, the wordpress part needs to be optional, ideally a plugin.
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