"trying to go this route without asking him" - who said anything about not asking him? Seems pretty obvious that this would be the implied first step.
Being homeless has given me loads of firsthand experience with how cavalier people are about completely disregarding the human dignity and agency of individuals they view as charity cases. So, I felt compelled to speak up and say "Please, don't view this as necessarily a great idea. There is more at stake here than money. Please, don't sell this man out because of his current financially desperate straits. That can make it impossible for him to get the life he desires and it can be done to him without his permission."
And the degree to which people here are shouting me down suggests to me that, no, most folks here wouldn't ask. They think it's a great idea. I am a lone voice on the side of respecting his dignity, personal choice and right to privacy first and foremost. And I find it baffling that people can claim well "Obviously, we wouldn't do any such thing" while doing exactly that thing. I have always found that baffling. But here it is again.
From your story, you appear to have a stronger connection to Ray's story then most folk on this site. Since you were in similar circumstances (without means), you have an understanding of how one can feel in that situation and your reaction is just, when viewed from that side.
On the other hand, people who read HN are entrepreneurial in spirit and instantly see it through their lense of "solving a problem". It is my opinion that most folk here have no problem doing what is necessary to get their story across or "sell themselves" to achieve a goal (within reason). Hence, to them, Ray's situation should be attacked with a similar POV as drumming support for a startup or idea.
I believe the misunderstanding comes from the way you are viewing Ray as a person and attempting to preserve his decency in the event he's not comfortable with some of the suggestions while others are viewing his situation as an issue to solve/conquer without similar experience. Both opinions are right but for different reasons.
Regardless, I'm glad that you had the strength to overcome your own hardships. Hopefully Ray has similar success.
My view is strongly shaped by the negative reactions I have gotten over the years on HN, where I have only sought to be taken seriously as an entrepreneur, but have largely failed in that endeavor. So I am very familiar firsthand with how much harm can be done to one's ability to support themselves when there is a lot of public attention given to them in a way that frames them as a victim, a charity case, and so on.
I have about six years of college. I was an award winning student. I am the top ranked woman on HN while homeless and, yet, I cannot get people here to take me seriously that the only damn thing I need in order to make my fucked up life actually work is arranging for an (adequate amount of) earned income that does not keep me ill.
In spite of the famous saying that There is no such thing as bad publicity, I have experienced firsthand that there absolutely is such a thing as bad publicity.
Entrepreneurs are promoting their work and accomplishments. It has a completely different impact on your life when what is publicized is how you have been a victim, how pathetic your life currently is and so on. That in no way convinces people to give you paid work, whether as an employee or a freelancer.
Also, his definition of dignity could be not being homeless or dependent on his kids. If that were true, it would be in contrast to your view on human dignity.
I suggested that he should be given options and not have publicity crammed down his throat as his only option. If he desires to go the publicity route, awesome! More power to him. But if he doesn't desire it and is given zero options, he may go with it because he has been in prison for 11 years and the world has changed and he has few connections out in the world and a fuckton of obstacles.