Ironically, the commentator who so roundly condemned personal (i) _________ was (ii) _________ to the point of bankruptcy—he himself was a reflection of an aspect of the ills that, in other areas, he railed against.

The first clue is the word "ironically" at the beginning of the sentence. This asks us to expect the unexpected. Now we know that he was himself a reflection of the ills he condemned. This indicates that he became bankrupt, due to some ill, and the only choice is profligate, as only profligacy - excessive spending - can lead bankruptcy and not asceticism or the irrelevant antediluvian. The only way the irony will be satisfied is if he had condemned profligacy in an individual's life, and the only synonym for profligacy in the choice list for the first blank is dissipation - the squandering of money.