The best way I can think of is to add a unique string to the end of the stylesheet include to get everything to update.
For example, if you are including it in the header.php file:
<link rel="stylesheet" href="https://wordpress.stackexchange.com/questions/62636/<?php echo get_stylesheet_uri(); ?><?php echo"?v='. time(); ?>" />
Of course that will keep it from being cached… ever. So you might want to turn it off and on. You could add a variable to activate it or you could tie it to wp_debug:
<link rel="stylesheet" href="https://wordpress.stackexchange.com/questions/62636/<?php echo get_stylesheet_uri(); ?><?php if ( defined("WP_DEBUG') && ! WP_DEBUG ) echo '?v='. time(); ?>" />
Or just comment it out when you are done:
<link rel="stylesheet" href="<?php echo get_stylesheet_uri(); ?><?php #echo '?v='. time(); ?>" />
You can use all of those if you are enqueueing the styles as well.
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