re: Need some advice/therapy - this looked like right forum

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You are right about the lifestyle. I think some people don't mind it.

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Don’t mind it? No kid. They fricking LOVE it much better than the alternative. They tried the alternative and it was not a good fit for them. They hate it when other people get high and mighty and tell them what to do. That’s why those who aren’t mentally ill are homeless. They don’t want to take orders from other people and they don’t want to make responsible choices - they just want to get by. But they know they have to play the game in order to get their handouts.

Your real problem is the guilt you carry. You’re insecure for some reason. Look at this last contribution:

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I gave her the print out just to show that I care. She thanked me. I included some phone numbers and a note.

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Get introspective. What void in your life are you trying to fill by believing your kindness will change the path of someone who is fully committed to this lifestyle?

I’ll credit you for having a good heart. But get more selective about the investment of your time and money. Try Habitat for Humanity. You’ll find more people who are committed to turning things around and will show genuine gratitude for your time and money to unselfishly help them.