We've got your back. With the Tough-O-Meter, you'll know whether to bring extra layers or Swiss army knives as you summit the literary mountain. (10 = Toughest)
(4) Base Camp
Sure, there are some Yiddish words and maybe the names are a little complicated to say out loud, and you should probably at least have a sense that it wasn't so super-awesome for Jews in turn-of-the-century Russia, but honestly? It's a totally straightforward narrative with reasonably modern values and ideas.
Like, check out this sentence that we plucked out pretty much at random: "With a little help from God, there I was penniless, poor as a beggar, with a wife and kids, starving to death three times a day, not counting suppers, may it not happen to any Jew" (2.3). Depressing? Yes. Difficult? Not so much. No problem just reading this thing straight through and figuring out some context as you go.