Yes, but do any of them have a cancelation penalty that goes into effect the second you press the " Book Now" button as we've been discussing?

All of my current bookings that I hold have a cancelation policy of between 11:59 pm day prior to arrival to 15 days prior to arrival. I've also held those with 30 day cancelation window and seen some with 60 days. Even if I've booked a prepaid non refundable rate, I had 24 hours to cancel.

I've never had a booking such as the one discussed here where you can prepay with points but the cancelation policy of 25% percent penalty in cash was immediate. OP didn't either ever have one it seems and was understandably unsure of what to expect. It's good to know that there is no hold done for that 25% penalty (but still doesn't make it less punitive if it does get charged in cash upon canceling a points reservation instead of paying 25% of your points which some expected to be the case).