“A fair bit of support and free services” != a home, so it should be unsurprising that the homeless remain. Getting a job that can afford a home is hard enough if you already have a home. Without a home at all, getting a job is just unrealistic.
You can say all you want about Castro, but he did in fact eliminate homelessness in Cuba.
You can say all you want about Castro, but he did in fact eliminate homelessness in Cuba.