"He appears to have no empathy for people who lost everything by doing the safe thing: buying a house, working a job, and living the dream."
How is buying a house the safe thing? A house is an investment and there is risk associated with all investments. If you aren't willing to take those risks, you shouldn't buy a house. Renting is still a viable option.
"Wall Street getting a bailout while average people are told it's unpatriotic and un-American to ask for help"
So two wrongs make a right? By wanting help you are just legitimizing the bailouts.