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Whether Padre Pio said it or not (I think he didn't), there is nothing in tradition to show this practice at all. It is an innovation.

You're an utter moron, on just about every subject that you post about.  It's already been explained to you that it's a simple truth of metaphysics that God is outside time, eternal, and that past, present, and future are all present to Him, that as a person lay dying He knows all the future prayers that would be offered just as much as the present prayers an the past prayers.

Do you deny this?  If you do, you're a heretic (in addition to your other heresies).

See, you don't even address the points, but you regurgitate and vomit up the same crap over and over again, since that's what stuck in your pea brain and you cling to it simply because you want to.  Those who use their intellects will seek the truth by actually applying reason to it.

Answer the question of whether future prayers are present to God and that He can know them and see them up front.

True or False?

Then, answer the next question ... has God ever regarded future merits?

Yes or No?

If you say no, then you're also a heretic, since that's central to the dogmatic definition of the Dogma of the Immaculat Conception, since Pope Pius IX explained the rationale for it in those terms.

So you must answer that God can regard future prayers.  You must answer that God has done so at least in one known case.

Consequently, in order to rule this out, you'd have to commit two heresies.  There's nothing to rule it out.

You also apply a completely idiotic notion of "innovation", as if something had not been revealed explicitly and believed from the very begginings of the Church in its precise form, then it's "innovation".  Well, that's what those who attacked Papal Infallibility claimed, since you can struggle to find explicitly formulations regarding the notion for many hundreds of years.  Same was said of the Immaculate Conception, where the detractors made the same claim for the same reasons.

How about "Limbo"?  For the first 1,000 years of history, the notion did not exist ... but it was only later pieced together, first by Abelard and then articulated clearly by St. Thomas Aquinas, and then for about the past 800 years, very few do NOT accept it.  There's actually some room for "innovation", in the sense explain by St. Thomas et al, where you draw new conclusions from previous conclusions, where it does ultimately derive from Revelaed Truth, but that does not mean everything is explicit from the first day.  Those like you came along and attacked it as a "Pelagian fable", a heretical innovation ... and the Church had to step in and condemn their attacks against Limbo for having allegedly been an innovation.

So it's dogmatically true that God certain can and in at least one known case has regarded future merits.  I stipulated, of course, that we cannot know that God will hear them and apply them in every case, but then ... the VERY SAME THING holds of prayers offered in the present time.  I can pray all I want for someone dying or currently in Purgatory, but God does not always apply the merits of our prayers, for whatever reasons He has.  There are many for whom lots of people pray who end up losing their souls anyway.  But there's absolutely nothing to prevent God from heeding future prayers.  Period.  End of story.  In many cases, we could be praying for the repose of the soul of people who are in Hell, who were lost.  We're told that this possibility should not deter us, since with God, no prayers are wasted.  That also applies to this situation.  If we pray for the conversion of those who died in the past, whether or not they have any effect should not deter us from doing so, since, again, no prayers are wasted, and there's NOTHING contrary to Catholic doctrine about a possibility that they might have some effect.  In fact, to assert the opposite, that they CANNOT have any effect, you have to dodge committing two heresies to declare it an impossibility, and then claim to have your own private revelation to deny the God ever does so.  Just as those who may attempt to pray for people who died the past cannot prove that God will apply those prayers, neither can you demonstrate that He will not.  You assume that because a positive outcome to the question hasn't been revealed, that's tantamount to a negative outcome having been positively revealed, which is nonsensical, and more of your logical fallacy.  When something hasn't been revealed one way or another, it's in the real of speculation, and the Church permits speculation that does not run afloud of established Church teaching.

The idea that praying for those who died outside the Church and after their death (retroactively) for their conversion in private is good, but that if we all come together at the chapel under Fr. so-and-so to offer some prayers for the same persons is bad!

Scandal is a public thing, obviously, so as you say it is understandable that the Church has such rules against public prayer for those outside the Church in order not to promote indifferentism. Praying in private causes no such problem. There is no issue, Let's not make one! Whatever a certain bishop may have said in relation to a certain noble lady does not necessarily constitute Catholic doctrine, I am sure you would agree. So let us pray for all souls, living and dead, that God may show them His mercy. That is our part, leave the rest to God.