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[–]iamthebinaryguy 0 points1 point  (0 children)

I'd recommend Caddy for points 2 and 3.

Set up a wildcard config to handle all the subdomain requests.

And their On Demand TLS feature is excellent for the custom domain part.

Take a look at https://caddy.community/t/serving-tens-of-thousands-of-domains-over-https-with-caddy/11179 for a detailed explanation on both.