Your plan looks a little dirty. In the best case scenario, let's say you set up and use the simple Grunt task to minimize all of your CSS and JS that your Wordpress instance uses.
This means that you need to dig the code, find where each of your plugins extracts styles or scripts, disables them and reduces their use with Grunt. After that, you should pick up the last thumbnail file and re-enter it into your Wordpress instance.
Besides having to do a lot of custom coding, updating your plugins will give you a lot of pain.
To adhere to a scalable and convenient plan, I suggest using the BWP minify plugin , which takes care of your styles and scripts, it supports CDN.
Then you can use Grunt as a mechanism for checking the quality of the code. Uncss is a great tool to help you find unused styles. Grunt-usemin is a great solution.
Finally, since I see that you are ready to move on to the command line tools, I would really like to take a look at WP-CLI it is a wonderful command line interface for Wordpress.
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