... I'd have to question this approach to photography, which to me smacks rather too much of the d*****l way of doing things. Shooting lots and hoping for the best may or may not produce some good images, but is the generation of a good image by little more than a happy accident now and then really what photography is about? ...
Well, since Winogrand preceded digital, I'd have to say this isn't "the digital way" at all. I dare say that shooting lots is a learning tool, since if you have to develop all of it pretty soon you'll start to hone in on things you want to keep.
I understand all of the arguments for and against the digital folks, but I don't buy most of it. I shoot film, and I do not shoot digital. Why? Because I like film. In my mind at least, there's no better reason that can exist.
In the realm of "image making" (verses stricter definitions of photographs) there are a lot of technologies, most of which have successively brought the imaging techniques closer to the masses. Frankly, without this march of technology most of us here would
NOT be shooting any film at all. Without Eastman trying to bring film photography to the masses we wouldn't have any film, and don't kid yourself that we'd all be making glass plates. Without Eastman "photography" would be relegated to the world of lab coats. And without digital imaging I sure wouldn't have two spare 4x5 enlargers in the garage that were gifts to get them out of someone's way.
Snapshots, both film and digital, are what you are talking about in my understanding: images that are made without significant forethought about composition and staging. At the other extreme would be studio portraiture: tremendous effort to control lighting, posing, and every other aspect of the image. Most of us fall somewhere between these two extremes, including the OP's street shooting suggestion.
To answer you directly, yes, digital does make snapshots much simpler and less costly. But I don't think that means voluminous image making is necessarily unskilled.
I expect that after some time the OP will begin to get a significant portion of keepers in the endeavor. As the project continues s/he is bound to learn and improve technique, so the critical eye is bound to develop as part of the package. After all, we're talking about a person, not a street camera mindlessly taking pictures.