Since I don't claim to know the biking habits of the typical homeless individual, I'm going to assume it involves getting to a place and then back home. Home being a structure in a field outside of town, not where you'd be able to return the bike for credit. My understanding would be that these folks would need the bike to get to and from "work," each and every day. Based on a similar rental system I found online, the 24-hour rental is $24. Alternatively, an annual pass is $80. The problem is that the trips can only be 60 minutes each. Assuming the homeless camp is close enough to downtown, this might work as a way to get around once in St. Augustine. Not a bad yearly price to not have to worry about bike maintenance, anyhow. If you're homeless already, and now you can get as many maintenance-free trips on a bike as you can use each day, then $80 for the year isn't bad at all.
But wait, there's less. The yearly pass will need to be paid for with a credit card with a fob mailed to an address. So even if these ride share bikes makes sense to homeless people, it might not be something that can be purchased without the help of someone with credit and an address. It might seem like a lot of people would volunteer to do this, but any extra time or any damage would be billed to the credit card, so I certainly wouldn't volunteer my credit in the hopes that someone else will always return the bike in time (or at all). The Cincinnati bike share, for example, charges $1,200 for a bike that is not returned.
I have a $1,000 bike. At least someone paid $1,000 for it back in 1986. I picked it up amidst college moving day garbage at UW-Milwaukee back in 1999. It was already worth $0 at that point. I've used some tape to hold it together, but it's still worth about $0. Since I'm probably not the only person in the area with a worthless bike, I'm thinking a bike donation for the homeless might make more sense than saying they should be using tourist bikes. That's not to say that bike shares don't have a place in St. Augustine, just that it might be meant for rich tourists instead of homeless interviewees.
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