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Wow, so my understanding of the terms 'reverse proxy' and Tailscale must be wrong then, because I thought they were mutually exclusive. I'll go do some more research, unless someone feels like explaining how you can do both at the same time.
Also, I think the 'Risks' section of this page is informative:
https://en.m.wikipedia.org/wiki/Reverse_proxy
I think self hosting the proxy with the services at hobbyist scale mitigates most of the security risks. The single point of failure risk is another matter. I once had to effectively reverse-hack my services by uploading a Jenkins test job through an existing java project to regain access. Ever since then, I maintain a separate ddns address that's just used for emergency ssh access.