How is being homeless not a failure on multiple levels? You can be poor by choice and happy with it, I agree. But is any sane person homeless by choice? Not traveling, hermit, not able to function in society, or many other cases. Just wanting to live somewhere and able to do work, but not having a home. To me that seems like a failure on multiple levels: country - global situation that allows people to be homeless, local - no community support or path to employment or investment into people, self - well... unless we give some income to everyone, and you can't claim benefits for not being able to work, you're expected to work for a place to live.
Unemployed is an artifact of the economy. I'd like to be successful enough to be unemployed, but rich and not homeless.
It is a failure on many levels - systematic ones, mostly. But if you read OP's post as not singling out the failure as being personally and solely responsible for their plight, rather than as a systematic failure, then we might simply differ on reading it. Donating money to combat homelessness at a systematic level is (in my opinion) probably a good thing. I just didn't get that sentiment in what I saw, though I allow for the (frequent and possible) chance that I am wrong in my interpretation.
This is exactly what I wrote. Not having a community-level support for cases of "you screwed up badly" is a failure. Same for no benefits when "life screws you up badly". Not sure where you see the empathy failure.
Unemployed is an artifact of the economy. I'd like to be successful enough to be unemployed, but rich and not homeless.