How far do you take this?

I take "sick" in that verse to mean "extremely ill". I.E not common cold, but perhaps Ebola, TB or something else of that severe nature. I arrive at that conclusion because when Timothy was having stomach troubles, a relatively minor issue, Paul exhorted him to drink a little wine, rather than oil and prayer. Also, the image of "praying over" in my mind leads one to believe that the sick person is in bed and unable to move much due to severe illness.

If I ever got TB or Ebola, or anything else case I would want any born-again Protestant to pray with me, and the Elders of my Church or any other Church that I agreed with to use oil and prayer.

As for confession, I think that is something the Church does not do well today. In college I had ever increasing severe issues with porn and my recently born-again fundy Baptist self reached out to an older born-again 60-year old Professor at my college who went to a Non-Denom Conservative Chapel. For 2 years we would meet in his school office for a half-hour to hour for prayer and teaching. I also had special software on all my computers that would send suspicious screenshots to him and we would talk about them.

I love that man to this day and the Church as a whole is weaker for the lack of accountability and confession that we do. As you rightfully pointed out, confession is extremely important. God mentions it in His Word for a reason.

 

I wonder if the people that James was writing to (the 12 tribes) were unsaved Jews, Messianic believers, gentiles or a mix.

Would this have any bearing on the message of James.

I also heard Zodiahtes once say that the Greek word for "anoint" used in James was considered the rubbing of oil and was considered a routine medical remedy at the time as opposed to a special supernatural cure.

 

What if the answer is "no"?

7 And lest I should be exalted above measure by the abundance of the revelations, a thorn in the flesh was given to me, a messenger of Satan to buffet me, lest I be exalted above measure. 8 Concerning this thing I pleaded with the Lord three times that it might depart from me. 9 And He said to me, “My grace is sufficient for you, for My strength is made perfect in weakness.” Therefore most gladly I will rather boast in my infirmities, that the power of Christ may rest upon me. 10 Therefore I take pleasure in infirmities, in reproaches, in needs, in persecutions, in distresses, for Christ’s sake. For when I am weak, then I am strong.
- 2 Corinthians 12​