Very eloquent Roger. I agree.
If you see work in a museum, and its presence there makes you feel like "an uneducated man a bad photographer" a second trip & some reading might be in order. It would be a very easy answer if you were indeed both those things or if the work was indeed bad inscrutable or incompetent.
I think some photographs - Ansel Adams might be an example - read very quickly as lovely art objects.
Other works operate as documentary objects of an aesthetic concept. Their craft is in the quality of the idea, and the object then becomes illustrative of that idea rather than of an aesthetic or technical pinnacle in and of itself.
Her photos are random in that they attempt to document the loss of randomness in cities - the human hand creating out of necessity rather than mass marketing.
In the old days, NYC (where a lot of her photos were made) was a patchwork quilt of the efforts of "mom & pop" stores and solo businessmen to market their wares to passers-by through the use of signs, either created by sign-painters, neon makers, or a brush & bucket on wood.
Now we have a Starbucks on every corner. The signs and such are trucked in from somewhere, probably pre-fabbed in China, and each Starbucks looks (give or take a bit of square footage) pretty much exactly like the next Starbucks a block down the street.
What's more - stores now tend to look like other stores, because they are as mass produced as the products they sell. The decorations, the signage, the fixtures, etc.
The loss of randomness as exemplified by the hand-made sign or the individual store-front is what the work of Zoe Leonard both documents and laments. So in a sense, what might be missing technically is filled-in, as it were, by nostalgia. But I actually like her "hand-made" looking shots, because they reinforce the hand-made, analog (as she suggests) randomness that she is documenting.
The photos are as hand-made as what they represent.
Plenty of artists hire technical assistants (Chuck Close, Jim Dine, etc.) in order to get the technical appearance they want in an object. Leonard could have just as easily hired a photographer as a technical assistant and directed them to take Alec Soth-like images of each store front she selected using her framing and her compositional arrangement. So I think the look is an intentional choice, not an absence of skill. It re-inscribes its subject matter with itself.
There was a terrific show at the Tate a while ago called Cruel and Tender. It featured the work of a number of photographers who worked within the inherited language of the early catalogist, August Sander. Along with the work of Sander was shown the work of Robert Adams, Diane Arbus, Lewis Baltz, Bernd and Hilla Becher, Philip-Lorca diCorcia, Rineke Dijkstra, William Eggleston, Walker Evans, Robert Frank, Lee Friedlander, Paul Graham, Andreas Gursky, Boris Mikhailov, Nicholas Nixon, Martin Parr, Albert Renger-Patzsch, Thomas Ruff, Michael Schmidt, Fazal Sheikh, Stephen Shore, Thomas Struth, and Garry Winogrand.
I wondered then why no Zoe Leonard. I think her work would have made a lot of sense in among these other photographers, perhaps not as a technician (though again, I am of the mind that her output is purposeful in its technique ala Roger Vadim's differentiation above) but as a concept-driven expression.