is_home() in HTML head

both is_home() and is_front_page() works in the header or anywhwere you are using a theme template.

Most likely, the problem is because you’ve hardcoded this: /wordpress/wp-content/themes/roots/style.php

Try instead creating your url like this:

<link rel="stylesheet" type="text/css" media="all" href="https://wordpress.stackexchange.com/questions/85053/<?php echo get_stylesheet_directory_uri(); ?>/style.php?tcount=<?php echo $count;?>" />