timmies… your from canada eh? i'm so jealous down here in the US we don't have tim hortons and i get upset about it every time i go to a dunkin haha.
but as for the idea it's something i've been trying to do personally for a bit. Here's what i do.
Backpacks if i can find them at a donation store i buy them otherwise i just use a bag, it sucks a little more but it works. Most of the clothes i buy at a donation store too. I look for sale days and red tag days to get even more. Sometimes if you tell the manager what you're doing they'll discount a bit more too.
Bottled water is always something i try to include and toilet paper. And as for starting well just one person at a time, i find it easiest to try and strike up a conversation first and then go to your car or whereever and grab the bag once you kinda let them know what your doing.