Praying for the Dead?

A long while ago I was reading an article about the death of Harold Camping - the infamous predictor of the end times.  I left a comment on the article saying: "He was a strange and confused man, but we should pray that he finds rest with the Lord."

The reaction I got from the rest of the Christian audience was  .... unexpected.

Praying for the dead is a completely normal thing within Catholic circles, but is considered by many others to be bizarre and possibly heretical.  So what unfolded in that combox was a long, somewhat exasperating exchange in which I tried to explain the concept.

Why would one pray for the dead?

Short Answers: Repetitive Prayers and the Intercession of Saints

Dear Apologist, I was told that Jesus doesn’t want us to pray repetitious prayers like the Rosary. Is that true?