I don't know much about first editions--what I have I've picked up at library and garage sales, and we're talking one or two books. For the most part I've been satisfied with reissued editions.
Your list of interests is pretty diverse. I probably don't need to point out that one of those things (Kerouac) is not like the others! Also, there's a pretty wide historical range there--The Jungle is almost thirty years before the depression, and Kerouac almost fifty years later!
However, given what you like, you may want to check out the work of John Dos Passos. A lot of people like his Manhattan Transfer, but I'm more partial to the U.S.A. trilogy--it's pretty much the Moby-Dick of the twentieth century. He was kind of a despicable person, but after reading that it was very hard to stand in judgement of him. If you like Sinclair, and Steinbeck, you'll love Dos Passos.
Also, check out the Marxist noir work of Kenneth Fearing. The Big Clock is a slender volume, but really fantastic in its own way, and prescient of corporate thrillers of the 1980s in a lot of ways. It very much speaks to the anomie of industrial/late capitalism, though it's more contemporary with Kerouac than with the depression.
If you're feeling plucky, there's Theodore Dreiser--but he's perhaps a bit earlier than what you're looking at. To me, the crucial depression-era authors are Nathaniel West and Dashiell Hammett--but that's just me. Noir fiction is making a huge renaissance--it shouldn't be ignored, since it captures something essential about that time period.
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