use strict;
use warnings;
use List::Util qw/max/;
use Data::Dumper;

my %type = ( '*' => 'u', '#' => 'o' );
sub type { $type{ substr shift, -1 } }

my @lines = map { /([*#]*)(\d*)\s+(.*)/; $2?[$1,[$3,{value=>$2}]]:[$1,$3] } <DATA>;
my $maxlevel = max map { length $_->[0] } @lines;
while( $maxlevel ) {
  my @indices = grep { $maxlevel == length $lines[$_]->[0] } 0..@lines-1;
  while( @indices ) {
    my $end = pop @indices;
    my $start = $end;
    $start = pop @indices while @indices and $indices[-1]==$start-1;
    my $sublist = [ type($lines[$start]->[0]), [ map { $_->[1] } splice @lines, $start, $end-$start+1 ] ];
    $lines[$start-1]->[1] = [ $lines[$start-1]->[1], $sublist ] if $maxlevel>1;
    splice @lines, $start, 0, $sublist if $maxlevel==1;
  }
  $maxlevel--;
}
@lines = grep { $_->[0] } @lines;

print Dumper \@lines;

__DATA__
* list 1 unordered item 1)
* list 1 unordered item 2
*# list 1 unordered item 2 ordered item 1
*# list 1 unordered item 2 ordered item 2
*# list 1 unordered item 2 ordered item 3
* list 1 unordered item 3
** list 1 unordered item unordered item 1
** list 1 unordered item unordered item 2
** list 1 unordered item unordered item 3
**# list 1 unordered item unordered item 3 ordered item 1
**# list 1 unordered item unordered item 3 ordered item 2
**# list 1 unordered item unordered item 3 ordered item 3
* list 1 unordered item 4

# list 2 ordered item 1
#3 list 2 ordered item 2
# list 2 ordered item 3
#* list 2 ordered item 3 unordered item 1
#* list 2 ordered item 3 unordered item 2
#* list 2 ordered item 3 unordered item 3
# list 2 ordered item 4