I left California for good over a decade ago, and you couldn't pay me enough to live there anymore (clearly! lol). I left San Diego because it was crazy, with the income coming in, that all that could be done was to tread water. So, I left, and now live in Texas, and it will require some large amount of dynamite to dislodge me! I loved growing up in California, but times changed, and not necessarily for the better, as far as I was concerned. There are, of course, positives and negatives to living anywhere; even in Hawaii, a tropical paradise to many, there are drawbacks. For me, the cost of living finally outweighed everything else. I decided that I could miss out on what San Diego had to offer from anywhere in the country; I didn't have to live there for that. On the other hand, I was in a position to make that choice, and (luckily) profit from it; not everyone has that circumstance. I went to New Mexico, which was, financially and in other ways, a huge improvement! I really haven't regretted leaving, at any point...
There are any number of reasons for homelessness; assuming any 'one size fits all' is going to be wrong. Period. I've lived in my car, and come many a mile since then. My brother, on the other hand, refused to stop living in his tent, or get help, even after he got clean, and he died young, cold, and alone. Which of us is 'the face of homelessness'? Neither, Jack, and not understanding that is always going to be a problem. There are those who literally choose to be homeless, whether for mental health reasons, drugs, or just plain orneriness. There are those who are temporarily homeless, and make good when given the chance. There are those who don't want a chance, but only the freedom they feel on the streets. There are those who have had a run of bad luck, or a single crushing circumstance, that broke them financially. And there are more, too; there are no pat answers. Assuming that everyone wants or needs help is no more 'correct' than assuming that nobody deserves help; it's an assumption based on one's own biases, either way. Enabling really isn't any more morally superior than tough love, and tough love isn't morally superior to enabling, usually except to those doing one or the other...
I don't know that there is an answer. Jesus told us that the poor will be with us always; that clearly doesn't mean that we shouldn't care, but it should also tell us that there is a limit on what we can do. I'll say that I do have some issue with simply raising taxes to address the problem, but only because much of that money will inevitably be wasted, squandered, and misused by the politicians who take it, then use it for their own purposes (and that means those from either side of the aisle; pretty much every single one of them at the state level or higher has dirty, and bloody, hands).
I do know that any good, workable answer won't be easy; it may be simple, but that isn't the same as easy.