You are not looking at the whole picture. Lord Jesus was a tradesman for 30 years and owned his own home. He wore sandals. Poor people had no footwear. Judas did not steal it all. Only a fool does that because its too easy to detect. He did take money from the treasurey, yes. Why did Jesus catch a fish for the temple tax? Maybe He was just making a point that He did not need to take money from the treasury to pay His own way. We know very little of what Jesus and the disciples did. The gospels are just a tiny portion of the actual ministry of Jesus and the disciples.
Paul may have bartered tents, we don't know. He did ask the churches to take up collection for the church in Jerusalem. I get the impression that it was money, not goods.
We know from history that the typical wage for a manual worker was a denarius a day. People were not paid in food or clothes.
In the first days of the church, many sold their possessions to help the less fortunate. Ananias' sin was not to have the money, but to lie about how much he was giving to the apostles. If he'd kept all of it and not lied about it, he would not have been punished.