$re = '/^#+(.+)\n*((?:\n(?:^[^\n#].{0,2}$|^[^\n#].{3}(?<!<!--).*))+)/m';
$str = '# Style
This style is suitable for having the header as the front, and the answer as the back
1 newline
<!--ID: 1717098832201-->
# Style
This style is suitable for having the header as the front, and the answer as the back
1 newline
1 newline with blanks
2 newlines
2 newlines with blanks
2 newlines mixed blanks
<!--ID: 1717098832201-->
# Overall heading
## Subheading 1
You\'re allowed to nest headers within each other
1 newline
1 newline with blanks
2 newlines
2 newlines with blanks
2 newlines mixed blanks
## Subheading 2
It\'ll take the deepest level for the question
1 newline
1 newline with blanks
2 newlines
2 newlines with blanks
2 newlines mixed blanks
## Subheading 3
It\'ll even
Span over
Multiple lines, and ignore preceding whitespace
1 newline
1 newline with blanks
2 newlines
2 newlines with blanks
2 newlines mixed blanks
';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php