My oh my, ..as far as tax collectors go, you asked the question, and i gave you a viable answer.
No you gave an incorrect or at lest very credulous and naive reading. Sure, prostitutes and tax collectors aren't well seen people. They are pariah. Nobody likes tax collector because nobody likes to pay taxes, especially when they are poor and the poor did pay taxes back then. Progressive taxation wasn't really a thing. That doesn't mean that tax collectors were especially corrupt; at time and under some administration, corruption was rampant, but not so much during the life of Jesus. When Christianity started to organized itself and the Gospels were written though, corruption and shady monetary practices were far more common. These two events are 50 years apart though.
As far as sin is concerned, and what Jesus denounced, it doesn't matter the sin, we where referring to Jesus differentiating between the sinner and the sin, which is what you discredited him for - remember?. And nobody said anything about prostitution, REMEMBER????Anyhow, you don't sound very serious epronovost.
Actually, yes we were specifically talking about Jesus being tolerant of others by going on and dining with the very unpopular tax collectors and prostitutes. These two profession were presented specifically as "sinners" or at the very least, people of ill reputation and Jesus was not opposed to rub shoulders with them even though he certainly did not condone their profession and behavior as you demonstrated. He referred to them as "sick" and in need of spiritual healing.
I personally think that differentiating between the sin and the sinner is more often then not pure and simple pedantry. Since a prostitute and a tax collector cannot stop "sinning" then they will not perceive nor feel any difference in your behavior and since they can't feel what you feel since they aren't telepaths the subtleties of your inner feeling toward them will be lost and thus completely irrelevant to them. You might as well hate the sinner and the sin equally and they wouldn't see much of a difference. If imagined or dreamed crimes aren't real, neither are imagined or dreamed virtues.
The big exception is of course if you develop a very close relationship in which there is a shared sense of intimacy and in which such subtleties can come to the fore. Since Jesus was dining with such characters, we can see at least an attempt from him to become intimately friendly with them, but sharing diner, washing feet and hanging around such people doesn't make you intimate with them.
My rejection of Jesus as a man of especially good character, at least in his portrayal in the Gospels, is the fact that its all presented in a very superficial way. Prostitutes and tax collectors are presented in those stories as obviously despicable and detestable people, amongst the worst people to hang around with. For a normal person, it would be a shame to be seen around such company in any friendly way and having a prostitute or tax collector in your direct family is certainly even worst. This despicable nature is important as its used as a device to raises Jesus' character. I personally see this as a blatant and unjust trick. Neither tax collector nor prostitutes, especially prostitutes, should be seen as despicable and detestable. Condemning them is wrong. What is wrong is corruption, or misappropriation and misuse of public wealth; what's wrong is sexism, dire poverty and slavery under which prostitute fall victim off. The parable of Jesus dining with prostitutes and tax collectors is used to raise the character of Jesus, the protagonist, but it in doing so diminishes and harms the dignity of innocent people whose dignity is already attacked unfairly by their own society for no fault of their own; they are scapegoated for larger more complex problems.