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I've been dumpster diving several times. Dumpsters with food tend to be awful - they smell, have flies, mold, and grease everywhere. If you want free food, just go to a programmer meetup and eat their free pizza.

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Or Costco for really cheap food, even if you're not a member (I am one, FWIW). They don't require a membership card to go in through the out-door (because this is how you reach the customer service desk to sign up for a membership), and at busy times walking in through there is completely painless. The food court is in that same (post-checkout) area near the out-door, and also doesn't check membership. Most of the food is a decent value, but in particular you can get a huge all-beef 1/4lb hotdog and a fountain drink for $1.50, or their "chicken bake" for $3. I don't know why more non-members don't take advantage of it. They'd probably change things if too many people did, because they can't be making any money on those two items in particular.

Costco tend to be located in areas not conducive for someone to go grab fat food though. It's not really worth the time and effort if you need to drive and take an hour to get a cheap hotdog

The season helps. Natural Grocers tends to put a lot of their food in a compost can next to their regular trash can. If you go there in late fall when the daytime temperatures are above freezing but the night-time temperatures are below freezing the flies aren't bad and you can find some fresh produce before it's been harmed by the frost. I still have a cutting growing in my kitchen from a "live basil" that we found there a few years ago.

We'd also find whole, healthy avocados and stuff there but we left those for the homeless.

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