Unless being on “the streets” means running with gangs and/or living in a slum. I’d rather spend those years in jail rather than watch my friends get shot (assuming that I’m stuck in this environment and have come to the conclusion that murdering is bad, revenge is unsatisfactory, etc).
Though I can’t imagine a situation where a person is rational enough to choose jail over the streets but not rational enough to find another way out of his current situation.
I think Wozniak is only evangelical about the Uberman schedule being a horrible idea. He states in his 2010 update that the Everyman 3-hour core sounds “pretty sustainable”.