I think cheating is a two headed monster, especially from person to person. And then there is the whole debate on whether your are "Paleo" or "Primal" and all that rhetoric, and there are some areas where the communities clash.
No soap box to stand on, but I rarely cheat. But I guess I consider myself Primal+Dairy per se.
If a strict Paleo person looked at my diet, they probably could light me up on many different things. I have grass-fed cream in my coffee nearly every morning, I drink 10oz of grass-fed milk post work out ( 3x a week), I still use a bit of condiments that have cane sugar in them, sour cream with mexican dishes, a bottle or 2 of wine per month, and I have the occasional handful of berries once or twice a week.
I do not have any immunological diseases or any negative reaction to the dairy that is currently in my diet, so I continue to supplement with it, smartly of course. BUT, there are some things I have cut out of my diet for good and will never go back to: ALL grains, ANYTHING with HFCS/CS, all diet sodas, most nuts, legumes.
So, in the end, when I do cheat, its usually with things that are still Primal/Paleo, I just have a little bit more of them. So if I feel like I need a reward, I'll eat more berries, or have more sweet potatoes, or have a little bit more wine.
I've been following this path for just a little bit over 10 months, with fantastic results. Could I be further along without the dairy, wine, or fruit? Maybe, maybe not. But my meals taste great, Im in ketosis on a daily basis, its convenient, and there isn't much thought involved.