I think that kind of ような would be shorthand for ような気がする. Maybe a bit silly, but the clearest example that comes to mind is here:
Code:
ええっ、胸が大きくなる方法が分かっちゃったの!?聞きたいような、聞きたくないような……
(you can Ctrl+f on that page for a sound clip to hear the tone)
So the meaning would be fairly close to what you inferred (though I wouldn't use 'of course' for やっぱ - personally, if I were approaching that passage, I'd want to have some element of hesitation in between those two lines, as he steps forward with something of an idea then doubts himself and pulls back.)
As for 境, I'm not really sure here. Maybe it's the border that marks where he went wrong and he's trying to think of the reason for punishment but is ultimately unsure? I don't really have much to back that up, though :V
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