It is pretty easy to become homeless in high rent areas like the west coast cities. An interesting side effect is that adjacent smaller cities also have high rents. For example, Bremerton, which is a ferry ride away from Seattle, has very few reasonably priced studios or one-bedrooms. Most are priced like in Seattle, and there is very little inventory. Prices at the high end do go higher in Seattle/Eastside, but at the low end, it's about the same. But wages are lower in Bremerton. So it is quite a squeeze for people earning on this side of the water.
I think that instead of concentrating businesses in the high rent cities, move them out to smaller, more inland communities. Reduce the demand for housing in the concentrated cities, and put jobs in currently unfashionable towns. Where the jobs are, people will follow. Where the people with steady income go, amenities and restaurants etc will also proliferate.
As for beggars, I never give. One time, twenty-five years ago, there was an able-bodied guy out begging in front of the supermarket near my teahouse. He came in later to turn his collected change into bills. He made more per hour than I could pay my workers, and I paid about 25-30% over minimum wage. I vowed then never to give to anyone.
A friend of mine in Pakistan only gives to old women. Anyone else begging is a fraud, he says, but old women have the least protections and resources.