You have my support and commendation. I'm a fellow Portlander (I believe we briefly met at the Portland meetup?) and have been doing much along these same lines myself:

https://steemit.com/charity/@alexbeyman/warm-winter-gloves-for-the-homeless-bros-aka-hobros
https://steemit.com/charity/@alexbeyman/operation-cozy-toes-for-the-homeless-bros-commence
https://steemit.com/charity/@alexbeyman/care-package-3-0-now-with-more-goodies
https://steemit.com/charity/@alexbeyman/care-package-4-0-is-complete-and-ready-for-distribution
https://steemit.com/charity/@alexbeyman/always-look-for-the-helpers-my-chance-discovery-of-the-free-hot-soup-organization

If ever you'd like to collaborate on a charitable endeavor, hit me up. I admire your passion to render aid where it is needed. The organization introduced in that last link may have use for you as well, they're already doing more or less what you aim to and run a very tight ship.