This isn't all that hard - you just use a custom sort and prioritize your comparisons by checking for special values first. In this case I use a set of regexes as hash keys and provide a default (3) for the cases that aren't covered. This example steps on the values $aKey, $bKey, $aPri, $bPri - you could modify the code to eliminate the temporary variables.

%sort_priority = (
  qr|^/etc/init.d| => 0,
  qr|^/root|       => 1,
  qr|^/usr/bin|    => 2,
  qr|.?|           => 3
);

@new_array = sort
  {
    # Get the matching keys
    ($aKey) = grep { $a->{'path'} =~ $_ } keys %sort_priority;
    ($bKey) = grep { $b->{'path'} =~ $_ } keys %sort_priority;
    
    # and now their priorities
    $aPri = $sort_priority{$aKey};
    $bPri = $sort_priority{$bKey};

    # Now compare based on priority then value
    ($aPri == $bPri
     ? $a->{'path'}    cmp $b->{'path'}
     : $aPri <=> $bPri)
  } @array;
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Update: And of course I forgot that it's a bunch of hash references. Now $a and $b are properly dereferenced