Specifically about those scandalous meals:
“Most writers now agree that eating with ‘sinners’ was one of the most characteristic and striking marks of Jesus’ regular activity. This would not have been of any significance, of course, if Jesus were acting simply as a private individual. But when it is allied with the claim, made in praxis and story, that Jesus was inaugurating the long-awaited kingdom, it aroused controversy. Jesus was, as it were, celebrating the Messianic banquet, and doing it with all the wrong people.” [NT Wright]
And, of course, the tension we find here between the official representatives of 1st Century Jewish orthodoxy, and those disreputable people accepted by Jesus… has continued to be a feature of Christianity, in that it implies a deep suspicion of the judgements of the rich, the powerful, and those prominent in the Church– continually holding up the likelihood that God, like Jesus, sees things quite differently.