So, I am reading this Feat and it seems as if even if you miss (failure) the Strike, the Target is still Flat-Footed?
And, also, if you are Small and Target is Medium (or larger) does that mean the Strike fails and the Failure kicks in; making Target Flat-Footed?
If you miss you make your opponent flat-footed.
Press feats (which Brutish Shove is) also specifically call out that their failure effects don't work on Critical Failures. I think all the feats w/ a fail effect are Press.
The Strike portion makes no requirements re: your enemy's size. You still do the damage as normal, you just don't get the bonus effects, at least not from hitting.
So it's kinda funny you do get one when you fail to hit; you would still make the larger target flat-footed. Seems like a loophole, but minor.
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Note that this has the Press Trait, so you can't use this as your first attack of your turn.
Actions with this trait allow you to follow up earlier attacks. An action with the press trait can be used only if you are currently affected by a multiple attack penalty. Some actions with the press trait also grant an effect on a failure. The effects that are added on a failure don’t apply on a critical failure. If your press action succeeds, you can choose to apply the failure effect instead. (For example, you may wish to do this when an attack deals no damage due to resistance.) Because a press action requires a multiple attack penalty, you can’t use one when it’s not your turn, even if you use the Ready activity.
Since this needs to be at least your second attack of the round and the flat footed effect only lasts to the end of your turn, the 'failure benefit' from it is extremely short lived (maybe two attacks if you are hasted, which would still be at a net -8 to hit with the flat footed status included)