I'm going to speculate on the Heather situation - I don't know what their contract states, but they have direct experience dealing with private information leaking when it shouldn't, and I imagine they're tailored and specific in their contract about it. Owning up to the risk is what saved Heather, IMO, and she was strong enough of a team member, dancer and ambassador that they chose to keep her on the squad but out of the limelight, so to speak. The risk today of leaked photos/videos/private anything is as strong as it's ever been, and social media is even more prevalent than it was several years ago when the big celebrity hacking scandal happened.
Paige also broke the rules about fraternization, but she was extremely discreet. For all I know, TPTB might have known it was happening, told them to stay quiet about it but if it leaked, they would have to release her. I think it depends on the maturity of the cheerleader, the infraction and how the cheerleader handles it.
Jenna casually dating Dak (or whatever their situation was) is one thing in private, but Holly hooking up with Zeke, going to clubs in Uptown where there are four million cell phone cameras and paparazzi? So completely idiotic I can't even wrap my head around it. Zeke was getting A LOT of negative attention for his antics back then. I wonder if that's editing magic - Kelli might have said "OMG Jenna, there are cameras everywhere, you know Holly is out there flaunting this rule breaking and drinking as a minor, and do you just let your friend jump in front of a car???" (Or whatever it was she had said.) And of course editing would just tell us the snip.
Who knows, really, but these are real people in real situations with cameras and editing. So I guess the editor knows best 🙂