These factors should allow the shite to execute the technique with little or no pain, if so desired, for demonstration purposes. And, based on my experiences taking ukemi for Yoshinkan practitioners, that is the case.
That is exactly the way Kanetsuka Sensei does nikyo ura - not surprising, given who his first teacher was…
All the Aikikai Hombu shihan I have come across, as well as Saito Sensei, tend to bring the hand into the shoulder to deliver the pin, even from shomenuchi and yokomenuchi. Kanetsuka Sensei's argument for not doing this (except where the attack is a shoulder grab in the first place) is that when the attacker has a weapon it is quite dangerous to bring that hand straight into the body.
Oh, and his nikyo is extremely effective, without inflicting much pain at all. The sensation is more of being knocked to the ground by a blow to the whole body simultaneously.