The Apache stuff I learned like 20 years ago still works - especially for not-huge sites (<600RPS). Point being, once you get this sys-admin task done it's super repeatable (regardless of server). And from one, moving between isn't that hard either. Dozens of personal services can run on a $5/mo VPS. One I have now is nginx to SSL terminate to 8 backend docker-things

Good pun +1 for that.

I recommend nginx or Apache for the learning exercise. Then go with whatever best suits your use case. My rule is choose that which fits the objective and which doesn't overburden with cognitive load. So I don't use Apache for anything and sometimes just use python's built in. suitability for purpose and usability is what counts for me.