If you spend too much time questioning the "Why's" and "What if's" it will drive you nuts.
Let me help you out with the 180 thing...the 180 is for YOU. Not her. What does Broken want to do for himself to show that he is changing/improving for the better? Whatever you decide to do for Valentines Day should not be considered a 180. If you want to do something like you always do, then do it with a NO EXPECTATION APPROACH. In other words don't expect any magical change of feelings or for it to be reciprocated.
And if you think it's going to ruin your day in any way, then it might be best if you don't do anything at all. This is trial and error. If something works keep doing it, if it doesn't...stop.
My apologies for not reading your whole thread. Just saw this and I hope the little I offer helps.