Well to put it as succinctly as possible it is flawed because progressives fundamentally believe that fairness is measured in equality of outcome rather than equality of opportunity.  Many of your wishlist items show this, and I may even agree to some extent with some of it, but not to the ends that progressivist take it.  You want big government to solve all your problems and since you need money for this you want to take as much money from the top earners in this country as you can.  The fact is that the top 1% of this country earn almost 20% of the gross income and pay almost 40% of the federal income tax so they are paying more than their fare share.  What you want to do is punish people for prospering to pay for those who refuse to.  Basically inequality and inequity are not the same thing.   There is upward mobility in modern day America, this isn't the dark ages were you were born into a social class and into that social class ye will stay.  But, you have to work for it, people working at McDonalds shouldn't make $15 an hour because they don't deserve it.  Those jobs are menial in nature and weren't meant to support a family, they were meant to support a teenager or college kids and give them some spending money.  I worked those jobs in college and earned a degree because I wanted more for myself and found a way to get it, and trust me it wasn't easy but I busted my tushy and payed for that education.  But, I am no superhero, I wasn't the beneficiary of some made up white privilege, anyone, regardless of their gender or race or financial circumstances, can do it if they want to put in the effort, but don't come and take the money i earned to give to those who don't want to put in that same effort.  Don't take my money to pay for other peoples bad decisions.  Welfare should be a safety net, not a way of life.  This country is becoming one of dependents rather than citizens.  

There is a difference between trying to be rude and letting a concern for hurting someones feelings prevent you from speaking the truth or taking a necessary action.  That is not to say that Officer Libtard over at the PCPD doesn't go overboard and get down right annoying sometimes.