No doubt, I've been spoiled over the years since almost all my CR-1s cleared weeks before my flights. Nowadays, it's right at the gate and take your chances with the seat.
I will continue to use CR-1s simply because the 500-mile certs convert to RDMs upon expiration. I have used 500-mile certs in the past but only when I really didn't care if it cleared or not such as on a redeye flight from HNL.
But you raise a good point as to whether one should shift upgrade instruments inside the 100-hour window.