I do different packs for summer or winter. I usually also include personal hygiene stuff, baby wipes, nutritious foods like jerky, protein bars, etc. In the winter especially I always include a new pair of socks. Cheap enough if you buy the bulk pack a Walmart. I also include $2 in each pack. Can't do much with 2 bucks but they might could make a phone call if they need to. Yes, there are still a couple of pay phones out there.
Living where I live we don't see too many homeless. The one man who was here and lived in a tent chose to do so. He was a drunk and received enough of a pension to have a home or rent ... but he was a drunk. The main thing we did for him was to watch out that he wasn't taken advantage of. A lot of unscrupulous folks would befriend him just to sponge off of his pension. We made sure he was taken to his Dr.'s appts. as well as we could. Just people in the community did this...not just his relatives. Also people from all walks of faith. We made sure he had enough to eat. He lived this way for at least 10 years until he had to be put in a home. He passed away about a month ago at the age of 82.