Some say Jesus was poor.The word-faith health-wealth preachers idiotically claim Jesus was wealthy and had a Cadillac (well, they don't say exactly this, but it's pretty idiotic nevertheless.) I think Jesus was well-to-do, a successful tradesman, perhaps a contractor.
If Jesus were homeless, where did his mother Mary live? As a good sonhe would certainly take care of his mother. This would include providing a place for her to live and for at least the necessities of life including the costs of regular pilgrimages to Jerusalem.
Jesus was well-educated and knew the scriptures very well; probably he had memorized them. Poor people likely had no such opportunities nor did they have access to the scriptures except hearing it at the synagogue or temple. He was comfortable conversing with the religious leaders implying he knew them growing up. I think his mother Mary was a consecrated temple virgin living among others like her and interacting with the priests and rabbis. She passed-on her vast knowledge and wisdom to her son Jesus.
Upon beginning his teaching ministry and gathering disciples, Jesus began to be considered as a Rabbi, meaning, teacher. But he was not a Rabbi before that. Some claim he had to be a Rabbi or he would not have been allowed to speak in the synagogues, but I doubt this. For example, if you go to a Sikh Gurudwara service as a guest wearing a turban, they will probably invite you to speak even if they don't know you. We are used to thinking of a sermon-based service in which only the leaders speak, but this is not necessarily the norm for all times and all places.
(Matthew 2:11) And when they were come into the house, they saw the young child with Mary his mother, and fell down, and worshipped him: and when they had opened their treasures, they presented unto him gifts; gold, and frankincense, and myrrh.
Often overlooked is what became of these gifts. Presumably they were very valuable, enough to make Joseph and Mary wealthy. Perhaps they lived off the money from these for decades. Perhaps Jesus used the money to pay for his ministry and to pay for renting the upper room. There is a tradition that Mary lived in a small room attached to the same building as the upper room.
Jesus looked after this mother Mary and somehow even provided for her while he was away on his travels. She may have followed him along with his disciples from time to time.
(Matthew 2:16) Then Herod, when he saw that he was mocked of the wise men, was exceeding wroth, and sent forth, and slew all the children that were in Bethlehem, and in all the coasts thereof, from two years old and under, according to the time which he had diligently inquired of the wise men.
It appears Jesus and Mary stayed in Bethlehem until Jesus was about two years old. Perhaps Joseph was able to find work there; perhaps his work near Nazareth had finished.
It's important to consider where Jesus lived in assessing his lifestyle...
Jesus was not shy about asking wealthy and influential people to put him up; presumably his disciples would stay there as well.