Don’t be paternalistic. Homeless people know how to spend money just like anyone else, and will spend it on the best thing for themselves because they are the only people who can validly make decisions regarding their own lives. If they need to self-medicate (“spend it on drugs”), who exactly are you to decide that is an invalid decision? And most likely they will spend it on things like food and clothing anyway.

Choose to help by giving someone some money or don’t. It’s a small individual action that may help someone else a bit. That’s all. If you care to make larger systemic change, you should really move on to organizing with homeless folks anyway; building networks of solidarity and helping to defend communities against the violence of the state and other bad actors. So maybe give someone a $20 but then sit down and have a conversation with them, and don’t think the one act of charity alleviates your social obligation to act with solidarity and help change society.

EDIT: PS - Your feelings might be “normal”, but that is only because they reflect the typical liberal propaganda perpetuated in society: that homeless people are somehow less human and less capable than everyone else and deserve their situation, rather than that they are simply victims of the capitalist economy that liberalism itself serves to uphold. These feelings shouldn’t be normal. So help work on them in yourself and in others. We all have things to learn and growth to do. Undo the conditioning this shit system has pushed at us since birth. Kill the cop in your own head. Then we can move on to the other ones.

We’d probably be willing to view ads if the experience wasn’t literally jarring.

Not me, sorry. Fuck ads. I’ve been ad-free for like a decade, and I’m not interested in regressing.

Hmm. Hate to be a downer, but that sounds like there needs to be a way for the service itself to block (ban) users and material, not for users to be able to block other users. So I wouldn’t be too optimistic about Apple’s response…