I’m with you on the timing issue, and there is nothing gained from commenting on the departed as to what they should or should not have done.
However, we have had many stories of heads of families pasing away and leaving behind uninsured (or underinsured)yesomim, and now there is a mad scramble to raise $ to keep the family afloat. True, talking about the need for insurance now is pointless (after all, it won’t bring poppa back) but it SHOULD be talked about so that uninsured people walking around today will see the consequeses of not taking their responsibities seriously.
Will the surviors be hurt by “insensetive comments”. Maybe. But if the next “besura raah” has a different ending because of the lessons learnt from the 1st tragedy, they family (and the mais himself) will have a degree of nechomah as a result.