functions.php not hooking up with style.css

Your theme has to call wp_head() in the head section of the html (probably best to place it at the end of it) and wp_footer() somewhere in your footer section. Those are mandatory function calls for all themes that want to be able to integrate with plugins and some core functionality like enqueuing JS and CSS depends on them.

If you do a “plain” HTML page, you have to manually insert the various CSS and JS into the HTML.