Going to go against the grain a little here and say, why bother? If you already have a background in Linux, that will get you further in your career much faster. My education was 100% windows/cisco, but I haven’t touched either in the better part of a decade since I’ve been working with mostly “web stuff” where Linux dominates.

Invest the time you would spend slogging through learning Active Directory and grinding MCSE into something useful like Docker, ansible, bash, infra-as-code, etc. It’s more fun, and it’ll make you way more money!!

That will never happen. SSL is based on trust, and the trust root will never blindly delegate to whatever happens in random LANs. Subdomain is 100% the right approach for internal network.

Drupal is a bit of a beast. It takes a lot of experience to keep one of these alive over time when major version updates will break plug-ins and custom code. I’d recommend either keeping it very vanilla or having a “guy” who’s either a drupal dev or has some experience with migrations. It’s fine to self-host, but handling those upgrades isn’t always easy.

I’d say try to push Wordpress as much as possible, and only go drupal if you absolutely need the features, but try to avoid customizations that add schemas or complex data structures.