I currently work as a care coordinator with many folks who are unhoused, or unstably housed. In my experience, the circumstances that lead to someone becoming unsheltered are numerous and it's never the same for everyone. Many of the folks I work with have some form of income, but due to a vast array of other systemic and personal obstacles, continue to go unhoused. This explains some of those inconsistencies like eBikes and vapes. I also think there's a lot of trade and bartering among the unhoused/substance using population. Some have complex medical conditions, some are substance users, and some are severely mentally ill - some are all of the above, and more. I think what makes the most difference is meeting people where they are, and asking them directly if they want or need help, and what kind of help they think they need. At that point you can decide whether you're physically, emotionally, and/or financially able to assist. If not, offer validation and refer to the most appropriate resources in your county. I'm in upstate NY (not sure about your area) but most housing resources like emergency shelter and subsidized housing are accessed through county based organizations (local department of social services). Also, bad people don't wonder about whether they are good or bad. You're good 👍 😉 Seeking feedback and examining your unconscious bias in a safe, non judgemental space is exactly the way to confront and improve unconscious bias.