I'm not sure I got the point of the OP. Is it just an observation? Is it a judgement call, bad, good or indifferent? Are there laws or social norms that prohibit homeless people from owning or riding bikes?

I believe the real issue is the increasing number of homeless that are on the streets. I have the opportunity to interact with homeless people on a regular basis. It is a problem without a good solution.

I've often thought about starting a weekly/monthly free bike repair day to help resolve safety issues. It would also be a good time to do a little education about bike maintenance, being seen, and rules of the road such as what side of the road to ride on.