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Selfhosted
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HTTPS performs two duties.
Your VPN provides the former but not the latter. That said the odds of there being an issue in this regard are so slim as to be zero, so you'll probably be fine.
It does though doesn't it? since every device needs to be authorized by me first
It can still have issues with potential attacks that would redirect your client to a system outside of the VPN. It would prevent MitM but not complete replacement.
Yep! It all comes down to your attack surface and how paranoid you want to be.