Hey Lex! Great ideas about the foam pad or biking shorts. I think I'll try the pad thing. I also just started trying to slow the reps down to put more stress on the core. I do alter the angle on the bench which cuts the reps down, which leads to less soreness.
I'm also doing Leg lifts, cable crunches, planks, and another one but I can't put a name to it. I usually do 3 different core/ab exercises for each workout so I do alternate. I guess hitting the high numbers on the sit-ups is more of mental thing. I also do alternate using a 25 lb/11kg weight plate on my chest periodically.
I guess I'm going to have to get out of my rut and try different things as you suggest. Thanks for the input! It is appreciated.