Work with css on WordPress and use Chrome too see the changes its a really pain in the ass. Second time cleaning the cache on 2 hours

Create a local environment with Mamp and use codekit or something for a build tool with auto-reload. Use fit and deploy it beanstalk to send up the files. Pull the data down with migrated-pro. Data down / files up. This is the best workflow you are going to get with WP.

Safari developer menu. Disable caches or empty cache. Pity that safari has gotten shit since Sierra. Still my favourite browser though, vivaldi looks good but it has some issues.

Or you can tag on a random number or some other shit to the .css file,
<link href="/stylesheet.css?<?php echo time(); ?>" rel="stylesheet" type="text/css" />

CTRL+Reload Button
// it will clear previous cache