Obviously the fact that it's translated complicates things, and I don't know anything about Danish. But I think the first sentence is meant to be a piece of folk wisdom akin to "Better to remain silent and be thought a fool, than to open your mouth and remove all doubt." That is, he's not really concerned with the relative proportions of regret, but with the idea that it's better (safer, shrewder) to keep your counsel than to stake out a position that might be contradicted. In light of the rest of the text, this is the reading of the line that makes the most sense to me: equivocation and bet-hedging in the name of worldly safety are a symptom of the sin of despair. Compare:

Possibility then appears to the self ever greater and greater, more and more things become possible, because nothing becomes actual. At last it is as if everything were possible--but this is precisely when the abyss has swallowed up the self.