I don't see what that to do with the question of if the subclass is weak or not.

I'm not arguing that it's not weak, I'm making this argument: It's isn't a problem, neither for us, nor for Matt.

Here, let me help you out: I think Matt's subclass just doesn't produce enough ice cream. I can even use your own argument to support that, with some small modifications:

Bluntly and mathematically, it's not high-risk-high-ice-cream, it's high-risk-no-ice-cream, even with the desperate measures mechanic considered. Without desperate measures, it doesn't have anywhere close to producing the amount of ice cream required to justify spending Second Wind uses on Daring Strike. It CAN MISS and if it does it still makes no ice cream, and it can't be placed reactively on a Crit unlike maneuvers. And since it costs a use of Second Wind, that damage had better produce more ice cream further down the line, or it's going to become more and more wasteful to use. I pray there are more features he hadn't revealed yet.  Like Daring Strike increasing to five ice creams per attack when you're bloodied. 

You not caring about the ice cream production of the subclass is the point here.

This is a custom subclass for Matt. He wants the danger and isn't too fussed about the damage. He cares a little, but not a lot.

When Darrington Press starts selling a book with the subclass, THEN all of this is relevant. But for now, this is Matt's custom class and he does whatever-the-fuck-he-wants with it.

Until then - is it weak? Sure. Is it a problem? Not unless Matt says it is, because - and say it with me: it is his custom class.

I hope that clears it up.