Desiree, I've wondered this myself in the past and have come to the conclusion that the 100 day cheat free challenge should be 100 days where you do not cheat at all.
However, I've set up mini-goals for myself and I use the cheat free bear clippie to help me keep track of how successful I've met those goals. If you want more details of my goals, let me know & I'll post them here.
I think you should use the cheat free bear clippie in whatever way motivates you most. There really are no hard and fast rules that I'm aware of. I say create your own rules and then let your conscience be your guide.