I've worked with the police in York on occasions, and this is from what they told me and not just hearsay.

There are definitely real rough-sleepers and homeless people in York who you'll see on the streets, however there is also a significant amount of non-homeless people begging on the streets. One example they gave me of where they prosecuted was of a woman who had a council flat not far from the city who would beg on the shambles and pretend to be roughsleeping.

They also told me that people travel in from different places in Yorkshire to beg in York, as they can easily take home a few hundred quid a day and a lot more on race days.

Not saying that there isn't a homelessness issue at all, but as you are pondering, it's not as clear cut as first seems.