Hey Sammo,
In Protools you don't have to chop/break the wav. You can just use clip gain creating new points like any other kind of automation.
It's still time consuming, all the same.
I used a demo of Waves Vocal rider a while back and actually found it to be really good! It might be worth a look.
I didn't buy it but right now I'm wondering why I didn't. Maybe I was broke that month. (odds are good).
Of course the "I don't want to hear it" answer is that you singer could most likely work the mic better if there's a pressing need for heavy automation,
but I concede that often there's still need for automation, regardless.
It's just one more thing to consider.
Welcome to HR!