I have heard this line many times over the years, and even now it still does not make sense to me. If one wants to help a prostitute, hiring them to turn tricks is not the way to do it in my view. Did you "care" about Barry? If not why were you trying to "help" him? Was it simply so that you could continue to have access to his body? If you did care about him, why were you patronizing his prostitution services thereby keeping him stuck in that dynamic?
I'm not questioning you so much as I the whole john/whore dynamic and the way both parties rationalize their own behavior (to themselves). 
How about, because I do not place a moral value on prostitution or personal drug use, like some people do? Because I don't believe that being a whore. or an addict, or an alcoholic, or even a convict makes someone a person not worthy of compassion? That I could ask the same question to anyone who cheers on their bodybuilding or athlete heroes to be bigger, faster, harder and stronger, yet acts all righteously indignant when they open their eyes and find out what they had to do to get big, fast, hard and strong?
I didn't "care" about Barry any more than I "care" about anyone else I meet whom I have dealings with in business. Unlike the "pathetic" schmoes at that board I refer to, I do not now and never have had any visions of sugar plums dancing in my head about these guys; similar to straight and gay men alike who like to solicit strippers and pole workers, I know they are who they are and do not think my relationship with them creates any special bond between me and them. However, that does not preclude me from treating them with general kindness and respect, as I would with anyone I have a business relationship.
One of my assistants at the office was arrested for DUI and spiraled into a bipolar depression. I am not her close friend and I owe hier nothing more than what the employment laws require, but I still was concerned for her as a human being and reached out to see if she was OK or needed anything in her time of difficulty. I didn't respond, "well, that's your shit. See you on the rebound."
You admittedly posted or were a member of at the same escort-client board you like to derail and deride. You consistently post photos (lurid and otherwise) and derive pleasure from the same big men who escort, use hard drugs and may or may not suffer from similar issues as some of these BBers who have succumbed to death or disease. Is your only difference between you and the schmoes, in your view, is that you do not spend money on them?
Barry's problems started LONG before he chose to escort. I am not and never try to be a Captain Save-A-Ho .However being kind to someone, even those who whore themselves out for money, never hurt.
I hope this helps you to understand my viewpoint.