i like how you personify Live... "fool Ableton" hah.

extending on the topic of voice range (changing the octave a melody is played in or transposing a sample) i agree that some voices will sound better in different registers but what might also be important to consider is what else is happening in the song in each range. this is also called "tessitura" and most clear productions do not have many parts conflicting or overlapping tessitura. Especially in a vocal piece, it helps a ton to leave a window open for the vocal range, most importantly the intelligibility range, in most cases 1kHz-4kHz (if you want lyrics to be understood easily ).

anyway, the idea of not using tools how they are intended, is a powerful one.