Having been around things for a good chunk of time, but not having to implicitly make "the call", here is some of my perspective.
Personally, I don't think I could in good conscience tell a kid (parent, or both) to intentionally "punt" a match. That being said, it would be absolutely irrational of me to say "we're not 'diving', period, end of story" - since the pragmatic goal of the district tournament is to get to the state tournament; it would be malpractice not to assess and examine all options.
Any internal conversation that coaching staffs have on this type of topic has to look at a wide range of considerations - examples being how much more manageable is the path with "diving" vs. "not diving", is there possibly a benefit to winning the tossup match to live with the consequence of not qualifying if that match is not won, is there possibility of the "diving" strategy not working out with a state spot anyway.
I've seen outcomes of wide range on this. The kid "dives" and gets to state, the kid "dives" and doesn't get to state anyway, the kid wrestles it out and loses the match(es) that modeling says they would, the kid wrestles through and wins the match that the diving would have avoided from occurring.
All that being said, I don't think one should pontificate with an extreme opinion on this, especially when they may or may not have been involved in one of these "crucial conversations". Along with the obvious of not being internal to the situation in question. WELL SAID!!!!!!!!!!!!!!!!