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FK: I've heard plenty of Catholics say that they pray to a certain Saint on a certain issue because it was his/her "specialty" and that the Saint would pray to greater effect because of it.

Yes, it comes naturally to pray for a saint known for some particular virtue. However, that the prayer of a saint has a greater effect is biblical, see James 5:16.

Here is that verse in context:

James 5:13-20 : 13 Is any one of you in trouble? He should pray. Is anyone happy? Let him sing songs of praise. 14 Is any one of you sick? He should call the elders of the church to pray over him and anoint him with oil in the name of the Lord. 15 And the prayer offered in faith will make the sick person well; the Lord will raise him up. If he has sinned, he will be forgiven. 16 Therefore confess your sins to each other and pray for each other so that you may be healed. The prayer of a righteous man is powerful and effective. 17 Elijah was a man just like us. He prayed earnestly that it would not rain, and it did not rain on the land for three and a half years. 18 Again he prayed, and the heavens gave rain, and the earth produced its crops. 19 My brothers, if one of you should wander from the truth and someone should bring him back, 20 remember this: Whoever turns a sinner from the error of his way will save him from death and cover over a multitude of sins.

I don't see how any argument could be made that this passage includes departed Saints. This writing clearly concerns only instructions to living people on earth. Do Saints confess their sins to one another in Heaven, for example? I don't think you would say that.

It is the righteousness of a saint that makes us expect greater effect, not his "specialty".

Then why are different Saints "designated" to different areas? Why would it come naturally as you say above if the basis is on general righteousness? I mean, if you had a medical issue would you seek the prayers of any doctors you knew ahead of asking other people for their prayers?

A canonized saint is certain to be in Heaven.

Why is a canonized saint certain to be in Heaven? I thought we were prohibited from judging the hearts of others (or knowing God's judgment of others) to this degree of certitude:

1 Cor. 4:3-5 : 3 I care very little if I am judged by you or by any human court; indeed, I do not even judge myself. 4 My conscience is clear, but that does not make me innocent. It is the Lord who judges me. 5 Therefore judge nothing before the appointed time; wait till the Lord comes. He will bring to light what is hidden in darkness and will expose the motives of men’s hearts. At that time each will receive his praise from God. (emphasis added)

I was sure this was God's territory alone.

However, it is not wrong to ask others to pray for your intention, dead or alive.

I'm sure Petronski would agree. :)

In fact, the only way for one to be canonized a saint is to have people pray for his or her intercession, -- pray, that is, BEFORE he is canonized, on the faith that he has heroic virtue waiting to be recognized.

How would that not amount to a human controlled popularity contest? I mean, along with the recognition of miracles and such, it sounds like a departed is elevated to the level of Saint in Heaven based on the decision of humans. Is that correct? Is your use of the word "Saint" simply a human description of a few of the departed, or do they have a special status in Heaven bestowed by God (because of human decision?)? I guess I don't understand if the term "Saint", as Catholics use it, presupposes canonization (such that "canonized Saint" would be a redundancy like "born-again Christian") or if it is possible to be an uncanonized Saint.

I don't see how any argument could be made that this passage includes departed Saints

It clearly speaks of situations that arise between the living. But it does not exclude the dead, and if they have eternal life as Christ promised them, then they are with us by default. By what logic shouldn't their eternal life be free from prayer? They are with God, are they not?

why are different Saints "designated" to different areas?

These are not formal assignments. You can pray across these "specialties". But , for example, St. Christopher served travelers in his life. So one who is traveling today expects St. Christopher to watch over him. He could ask anyone else, but we pray to saints because of a connection we feel in a particular context. If traveling, to St. Christopher, if arguing about theology, with St. Thomas Aquinas and St. Dominic, etc. Because you think that if they did a certain job or had a certain experience in life, they would be better suited to assist you with their prayer.

Why is a canonized saint certain to be in Heaven?

The Church examines his life and finds evidence of heroic virtue. That is what gets one to heaven. You do not judge others for things you yourself are liable; you can judge others positively all you want.

a departed is elevated to the level of Saint in Heaven based on the decision of humans. Is that correct?

Yes, in part. The Church needs to see a spontaneous devotion to the departed. Absent that, one would question that his virtues had a heroic, that is oriented toward the others, character. It is not enough to be popular, but yes, it is one of the prerequisites. Of course, nothing prevents us from lifting a saint from obscurity. For example, many victims of Communist Terror in Spain would have been forgotten if some Spaniards did not keep their memory alive, and now over 400 such victims are canonized saints.

It is entirely possible to be an uncanonized saint, -- everyone who dies and goes to heaven is a saint, but only few are canonized. This is why it is no contradiction with the usage of the Early Church to have canonized saints. If you beleive someone to be sure to go to heaven you can call him a saint. It becomes your private judgement and is, I think, a good thing. Note that canonization does nothing to the saint, who is in heaven in a state of supernatural happiness already. It serves the living by giving them a friend they otherwise would not know about.