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Is your church close to any of the other facilities available to the homeless? If not, getting to the drop in center could be a stumbling block to the folks sleeping in your church. Perhaps your church could partner with someone else in providing some sort of transportation, if anyone has access to a van.
My uncle lives in Eugene and lived on the streets for many years by choice - like you said, he didn't want to work for The Man. Now he lives with friends in a house so he's no longer homeless (and he's been living in the same place for awhile, I believe) - I'm not sure how they pay for things, though. Perhaps you could ask church members if they know anyone in a similar circumstance, people pooling resources and living communally. They might have advice.
I wish I could be more help, homelessness is a terrible thing. My brother was homeless before he died; he stayed with us for a month or so because we didn't want him sleeping in the park. He couldn't stay at the shelter because he drank. My sister lived in a homeless shelter for several months and then ended up working there and we've talked a lot about this topic. There are such a wide variety of causes that there really isn't a surefire cure.
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"They say that patriotism is the last refuge to which a scoundrel clings; steal a little and they throw you in jail, steal a lot and they make you king"
Formerly Medusa
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