Yes, Paul's asking others to pray for him is not an answer to a question about communication with those in heaven. It's an answer to the asked question about seeking for intercession.
With respect to asking for intercession, whether the person asked is on earth or in heaven is not to the point. So to raise the quite different issue of whether one can communicate with those in heaven is to change the subject from the subject of the question. IF, as was the case, the question is about intercession, THEN Paul's asking for intercession would put us where we have to say either that it is good to ask for intercession or that Paul erred (or we don't know yet). If we agree that it is good to ask for intercession, then we can examine the quite different question of whether we can or -- if we can -- should communicate with those in heaven.
Both points go to the question about asking for the intercession of the saints in heaven, but they are different questions.
Mad: “With respect to asking for intercession, whether the person asked is on earth or in heaven is not to the point.”
I must disagree with your contention. The primary point I am making is not whether we should ask for intercession, but to whom we ask. That seems to me the fundamental question we must resolve. The point of WHETHER we should ask for intercessory prayer seems to be universally accepted.
The bigger question is to whom we should ask for intercession. If I were to ask a known satan worshipper to pray for me, I would get a significantly different outcome than asking my pastor to pray for me.
I disagree with most of the posts here that claim “prayers” to saints are not really “prayers” but requests for intercession (its all very semantical and twisted). Paul was not asking the risen saints for prayer in the referenced passage, he was asking for prayers from fellow soujourners in faith - those whose faith could be built up by prayer.
When you truly begin to understand the purpose for prayer, the idea of praying to the saints becomes non-sensical. Prayer is not a means of notifyig God about a problem that needs resolution - do you think God is not aware of your needs or troubles? Prayer is not a conjuring nor tour de force. We are not changing God’s mind when we pray nor are we breaking any news to Him. Prayer is our means for developing a closer relationship to the One we pray. It is also a special means by which God sanctifies us and takes our focus away from ourselves (which we so rarely do otherwise).