That's exactly the problem. You can't make their lives more comfortable. You actually have to make their lives worse until they choose to get out.

I listened to a guy who actually ran homeless shelters in the UK and he said that you should never give money to homeless people because it allows them to stay out on the streets longer. Until they can be forced back to the shelters, where they will basically be forced to get counseling and drug rehab or jailed (where they will also be forced to at least get clean).