Why should we care what income level Jesus lived at?
There has been a lot of academic Biblical scholarship which points towards the idea that Jesus was poor, a peasant leading a revolt of fellow peasants. This then bleeds over into theological speculation, and has tended to be harnessed to a class consciousness, even class warfare explanation of the Gospels. Eventually stuff like this does, and has, filtered down into the pulpits.
But is it correct?
Dr. David Fiensy, retired Dean of the Graduate School of Bible and Ministry at Kentucky Christian University, author of half a dozen books on Biblical archeology (including the excellent Christian Origins and the Ancient Economy LINK) and participant in seven archeological digs in the Holy Land, especially in Jesus' region of Galilee answers that question in this short video.
Jesus was a 'tekton' a carpenter. As he points out, carpenters were more than handymen of craft workers, they were builders, often working with stone masons on frames, scaffolds, etc. This was not a life of poverty. It was better than the truly poor by far and usually better even than the life of a small farmer.
Was He rich? Not likely. He wasn't exactly middle class either because int eh 1st century Israel, there really did not exist a middle class, a rising group between worker and nobility. But there was a 'middling class' meaning someone richer than a peasant and poorer than the nobles. People of Jesus' background generally found themselves in that group.
Here's a short video in which Professor Fiensy explains these distinctions.