How to imitate CSS counters?

One way would be to range through the children of .Content or an outer Shortcode.

Here is a technique for counting the children of a Shortcode: Range over the children of a Shortcode - #6 by onedrawingperday

It can be adapted as needed.

The general idea would be to create the numbering within the scope of a: range $i, $e := $inner

$i stands for index
$e for element