This theory is always posted in these threads but there is no answer how come the places with the most expensive real estate have no homeless. Aspen, Hamptons, Malibu, Beverly Hills, Martha's Vineyard etc. etc. do not have homeless encampments, which should have been huge according to this theory.

The trick it uses is introducing a continuity with the "easier" term. There is no such thing in reality. If you have no income you won't be renting either $1000 nor $10000 apartment despite the former being "easier" to afford. And if you have income you will move to the housing you can afford and won't be hanging under an overpass just to piss off the landlords.