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#foreach ($strMess =~ /.*?\n(?=\S)/smg) {
#foreach ($strMess =~ /.*?\n(?=\S|\s+[^\n]+?:\n\S)/smg) {
...
   s/\n\s*/ /mg;
    push(@arr, $_);
}

Into the little hill
2-osainen lyyrinen tarina sopraanolle, altolle seka viidelletoista
...
09  9. Another very long stupid song title to be used as yet another
    dumb example /6:66.
10  10. Last fictive song title /6:66.

  1| Into the little hill
  2| 2-osainen lyyrinen tarina sopraanolle, altolle seka viidelletoist
+a
...
 14|     3. OSA BLAH BLAH BLAH BLAH BLAH BLAH BLAH BLAH BLAH BLAH BLAH
+ BLAH BLAH BLAH (09-10) /14:14:
 15| 09  9. Another very long stupid song title to be used as yet anot
+her dumb example /6:66.
 16| 10  10. Last fictive song title /6:66.