Also a part time admin who's done some of this. In our case, we were just setting up an https server and self-certifying. It was convoluted (to a non-admin) but we eventually figured it out until the TLS thing happened then the re-learning curve was high.
So, based on personal experience only;
- The admin help and targeted searches for information can get you everything you need.
- If you have a test environment, you can muck about without killing anything so if this is something you want/need to learn, play until you get it right, then do it in production.
- If this is low risk (i.e. it's OK to screw up your production environment), then play until you get it right.
- If you don't have a test environment and/or this is important and/or screw ups are not allowed, pay for a consultant; the cost of getting it right is FAR less than getting it wrong and screwing up your server.
Doug