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So, we are supposed to judge the heart of the deceased?  I always pray to Our Lady. If the person is lost, She will redirect the prayer to whom she sees fit. No prayer goes to waste. There are just some people whose condition at death you do not know.
Unless you are the strictest of Feeneyites and a staunch Jansenist, you don’t know for sure the person was a validly, practicing Catholic in the state of grace, don’t bother praying for them?  Is it not better to err on the side of mercy rather than judgment? 

We don't know ANYONE'S condition at death... period...and that will include ourselves when we die until Jesus reveals it to us.
We could be chained to someone our whole life or be a siamese twin and we still wouldn't know the condition of the other person's soul at death.

As for praying conditionally... if that were a thing wouldn't it be in at least one prayer book?

Just say, "I pray for the souls in purgatory, especially anyone I know and owe and love."

We don't know ANYONE'S condition at death... period...and that will include ourselves when we die until Jesus reveals it to us.
We could be chained to someone our whole life or be a siamese twin and we still wouldn't know the condition of the other person's soul at death.

As for praying conditionally... if that were a thing wouldn't it be in at least one prayer book?

Just say, "I pray for the souls in purgatory, especially anyone I know and owe and love."

1)All prayers are conditional on being God's will. As an example, I could pray for good health every day, and God's will could be that I stay in poor health during my life as a trial. 



2)Because you can't think of one, you think they don't exist? I will give you an example. During WWI, many french families didn't know if their loved ones were still alive, or not. Praying for their safety is conditional on them being alive, is it not? Likewise, praying for their soul is conditional on them having persevered and being in Purgatory (which, considering the horrors of WWI, was no easy thing). Moreover, there are many french soldiers who became devout catholics BECAUSE of the war, despite being lukewarm during their life. 

Considering the many levels of unknown in the equation, all prayers in this instance are conditional. Conditional on information that only God has. 

3)There is a difference between the Church officials (priests and so on) and laymen. Public liturgy for known heretics WOULD DEFINITELY foster indifferentism among the flock. When the souls of millions of people are at stake, would it be prudent to hold public masses for those people? The answer is NO. Of course the Church and the Popes (who are very careful about the salvation of other people) would give the best possible instructions in order to save as many souls as possible. 

However, if someone is already aware of the risks, and knowingly prevents the possibility of sin, and only does a private prayer with no risk of scandal, that is not the same. There is a difference between "most people", who usually are not theology experts, and someone who knowingly controls their prayer intents to ensure orthodoxy. Church officials, of course, are concerned about ensuring every person in their flock will be saved. 


4)Those are merely my attempts at understanding the motives of Church officials. I am only a layman , so what I say is far less important than what my superiors say. I believe that, both the letter of the law and the spirit of the law should be taken into account when looking at what the Magisterium wrote. 

5)The prayer you gave as an example "I pray for the souls of Purgatory, especially anyone I know and love" is already a conditional prayer. It is (theoretically) possible that not a single person you love is in heaven.