Do I actually need to link my theme’s style.css in the theme files

I would say: you should not use the style.css for the actual production CSS.

The reason is simple: minification. You cannot minify the content of the file completely, because WordPress has to read it. In my themes, I use style.css just for the headers, and I add a comment, explaining where to find the real CSS, so other developers don’t have to search too long.

Example:

/*
Theme Name:    My theme name
Version:       2013.08.24
License:       MIT
Text Domain:   t5_theme
Domain Path:  /lang

You will find the real stylesheet in css/default.css.
*/

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