In Heiwa's case I don't think it would work to require direct answers to specific questions. It's a foregone conclusion that he will either ignore or evade such a requirement. It's easy enough to do; he can just give a non-responsive or non-sequitur reply and claim to have met the requirement -- or just ignore it altogether. LO would have to ban him even though his behavior was not all that objectionable.
For me, the real issue is to prevent the repeated insults, jibes, and moderation attempts that raise the frustration level and threaten to produce angry responses. LO has been doing pretty well there, but it's a big burden on him.
How about this: set a fixed limit on the number of posts that will be suppressed due to those specific issues, say 5 or 10 from now on. Once he hits the limit, banhammer. As long as he can keep posting without violating those limits, we keep the chew toy around for general edification. But if he keeps up the snide stuff there's an end point for LO.