I don't allow free pushing. It's always got a downside. I'm lax about relabeling the conditions narrative aspect... for example, instead of Angry, call it distracted or frustrated for the scene...
One player declared as he marked the condition on strength, "I may pull a muscle, but I'm gonna hit!" (then rolled one over skill with the resulting disafvantage from it.)
The other thing is that I expect marking the condition for the attribute of the skill pushed; the push is at reduced odds due to the condition most of the time. (And, of course, the standard for all taken means 1d6 WP instead, and if all WP used, 1d6 HP.)
I do allow pushing in almost all situation, it will have a side effect. I expect the RPs to role play the disadvantages taken. An Angry RP might not just go back home to take a short rest, "it is not my fault that merchant is an idiot, let's check out the weapon at the smith now......"storms in to the shop and demands to try out that big ax!").
As to when the disadvantage (bane) is applied. Not sure I understood you correctly, but the disadvanatge is not recived until after the pressed role. So unless you already have a bane you will reroll with your full skill and
after that recived a disadvantage to an attribut.
I have ruled that you can only press a roll if you still can take a disadvantage, so when you have all six of them you can not press anymore. And yes this has come up, we had a very tough combat where more then half the group was maxed out......"broken unit".