Cutting Words is almost always better, just by the numbers.
This table gives the probability of meeting a given DC with a straight roll compared to advantage minus a Bardic Inspiration die:
Yes, this timing works.
Superior Inspiration triggers when you roll initiative.
Peerless Skill says:
Roll a Bardic Inspiration die and add the number rolled to your ability check. You can choose to do so after you roll the die for the ability check
As soon as (“when”) you roll the dice, you get a Bardic Inspiration die. This is before the time when you may ...