If you want to never allow someone to overcome their past, then be that way. In fact that makes sense as that is the right-wing mentality socially speaking.

I am a huge supporter of letting people change, especially considering he was not in control of which school he went or am I understanding it wrong?

First of all, he is not a socialist he is a social democrat who supports private industry as a concept but not as an unregulated 'beast to be unleashed'.

Secondly, since America is not as socialist-leaning as he wants it to be he has to compete in the environment that is more right-wing than the one where he wouldn't even need to house the poor (they'd be housed for by the government or some half-way negotiated funding program that is meritocratic and temporary-visa based so as to not need to deport them all).

Last but not least, the redistribution of wealth is what 'trickle down' economics is based on. It is not what Bernie's economic model was based on at all. It wasn't a matter of making everyone's income the same it was a matter of the richest having such ability to influence elections via the media and phone app ads (and potentially fake social media accounts if the Russian-hacker theory is true) that they can get whoever they want elected unless there's enough other rich people wanting another candidate elected. He wants to make sure they are never rich enough to do that on such a scale without us knowing and frankly so does Hillary no matter what you say about her. If it wasn't for Hillary and the investigations into Facebook (which have been proven true, Zuckerberg is only not behind bars due to good lawyers) you know what? I feel like I'm typing to a wall here, I know you're gonna reply some nonsense right-wing taunt to me so why bother.