Perhaps a bit more that the homeless pose complex considerations. Are they someone who had bad luck or someone who actively destroyed everything around themselves? If you help them will you waste your energy and in the end hurt them or will it actual assist? Will they be angry with you or even attack because it would be so easy for you to help a lot but you don't?
Self judgement over not immediately helping, self limitations in our faces (many of us are closer to homelessness than stability), guilt over not donating more, sadness over our judgments of the homeless, fear over becoming homeless, discomfort with smells or ideas of correlated behaviors, pity, incomplete information... the list of sincere challenges goes on and on.
I've got a sister who I love but deeply deserved to be homeless after hurting and spreading ruin on everyone around herself for decades. Anything you did to help she would use to hurt herself and others more. Most down and out people are not her. For those who had a bad circumstance, a leg up has additive economic benefit and benefits us all. Most safety net services are about being ready to support those who are ready to do exactly what you suggest. Many of the rest are there to help them survive to getting to that place.
Your final statement seems so zero sum. Our society exists because we find ways to make each other's efforts more productive and effective than they otherwise would be. We're all better off if being better off is scaled. There are defectors but also controls in place.
Imagine we live in a world where everyone is issued housing. To make that more sustainable, we create a lot of group housing. Now imagine that someone in that group housing gets it in their mind that it would make them a YouTube star to burn their house down live. They succeed in their arson and burn their house and the house of all those around them to the ground.
This person doesn't deserve to be without a home at least for a little while?
[Edit
I forgot an even more important class of individuals... The homeless we refer to as hobos (aka the intentional homeless population who choose it as a lifestyle where they are freed from the demands of society and in turn be undemanding upon society). Do not these people deserve to have their homelessness respected? They are a small portion of the population but it seems a valid life strategy and I have had a conversation with the man who described his homelessness in this way and claimed to have friends who felt similarly. Reduce your expenditures sufficiently and it takes very little investment income to have a sustainable life of no obligations. The ethics of economic rents aside.
Self judgement over not immediately helping, self limitations in our faces (many of us are closer to homelessness than stability), guilt over not donating more, sadness over our judgments of the homeless, fear over becoming homeless, discomfort with smells or ideas of correlated behaviors, pity, incomplete information... the list of sincere challenges goes on and on.
I've got a sister who I love but deeply deserved to be homeless after hurting and spreading ruin on everyone around herself for decades. Anything you did to help she would use to hurt herself and others more. Most down and out people are not her. For those who had a bad circumstance, a leg up has additive economic benefit and benefits us all. Most safety net services are about being ready to support those who are ready to do exactly what you suggest. Many of the rest are there to help them survive to getting to that place.
Your final statement seems so zero sum. Our society exists because we find ways to make each other's efforts more productive and effective than they otherwise would be. We're all better off if being better off is scaled. There are defectors but also controls in place.