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 "Hershel, I don't know how I'm supposed to tip you."

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Well, Lew, when in Rome!

I'm not sure if that was a joke or not. Is it a play on Romans giving blow jobs in exchange for goods and services? Because if that was a thing (I think that was a thing in the HBO series Rome), that could be the joke. And also if that is a historical fact, then I'm really giggling about Jesus saying, "Render unto Caesar what is Caesars." Because that's sort of like saying, "When in Rome!"
    But the problem is "When in Rome!" just means "Do things you normally wouldn't do when at home, as long as they're things that the locals commonly do, not suddenly become a serial killer or set buildings on fire." But I suppose because the Romans are practically interchangeable with the Greeks to morons like me, "When in Rome" just makes me think I should engage in sodomy when in Rome. Which is just a terrible thing to think, especially when I know for absolute fact that it's the Persians who were known for sodomy, according to one of Richard Francis Burton's endnotes in his translation of The Book of One Thousand Nights and a Night. The exact quote is offensive on many fronts but I'll quote it here so you know I'm only believing terrible things that famous people said a long time ago: "'Ghilman' are beautiful youths appointed to serve the True Believers in Paradise. The Koran says, 'Youths, which shall continue in their bloom for ever, shall go round about to attend them with goblets, and beakers, and a cup of flowing wine,' etc. Mohammad was an Arab (not a Persian, a born pederast) and he was too fond of women to be charged with love of boys: even Tristram Shandy knew that the two tastes are incompatible. But this and other passages in the Koran have given the Chevaliers de la Pallie a hint that the use of boys, like that of wine, here forbidden, will be permitted in Paradise."
     I mean, egad, amirite?! But he does mention Tristram Shandy so that's pretty postmodern, right?!

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 Darby, recognizing them as members of Bindlestiffs of the Blue A.C., a club of ascensionaries from Oregon, with whom the Chums of Chance had often flown on joint manœuvres, broke into a welcoming smile, especially for Miss Penelope ("Penny") Black, whose elfin appearance disguised an intrepid spirit and unfaltering will, and on whom he had had a "case" for as long as he could remember.

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"Bindlestiffs of the Blue A.C."
I'm fairly certain the "A.C." just stands for "aeronautics club" even though I really wanted it to stand for "antichrist" or "amazing Christ," seeing as how this club is made up of ascensionaries. I think that's something like "missionaries who descend upon you like vultures from the air." "Bindlestiff" is probably a derogatory term by now but it basically means a tramp or a hobo. You know, somebody who carries a bindle. These guys are just tramps of the air, flying around getting into trouble stealing pies from windowsills and destroying primitive cultures with their love of Christ.

"from Oregon"
I'm not from Oregon but I'm kind of from Oregon since Oregon was where my alcoholic father geographicked to after divorcing my mom when I was two. So I spent the odd weekend or two up there growing up. Now I live here. It's exactly the kind of place an aeronautics club called the Bindlestiffs of the Blue would be from. Except they wouldn't be espousing Christ's teachings now. Now they'd be spreading Marx's words and their balloon's gondola would be full of chickens.

"Miss Penelope ("Penny") Black"
This is the first knowingly female aeronaut! I bet Darby isn't the only aeronaut with a crush on her. Part of the reason men think women have their pick of any man they want is because so much gatekeeping is done on various hobbies and occupations. If you only allow one or two women into your club of dozens of men, the men are going to swarm all over the woman as a potential partner. And when she refuses them all, it isn't because she's some prude or cold hearted person. It's probably because the guy she's attracted to isn't attracted to her which means she's in the same boat as all the men attracted to her who she isn't attracted to! If you want more opportunities to meet a woman whom you're attracted to who is also attracted to you, let more women into your spaces! Or, better yet, get into hobbies or occupations that are typically considered feminine by society! Or, and this is a revolutionary idea, if you're a heterosexual man, maybe don't treat every member of the opposite sex as simply an opportunity to get laid!
    Why did I go on that rant? Who knows?! What I really wanted to say was that Penelope is a great name for a dame from 1893! And her surname of "Black" probably means something too! Like, "black" is the color of a moonless night so it's the opposite of "day" which we're apparently "against." It's the absence of light and light is (or will be?) an important theme in this book!

"elfin appearance"
This either means she's short or tall, depending on what kind of elves Pynchon is talking about. Probably short since this moment is pre-Tolkien (not pre-Tolkien existing since he was born a year previously! But definitely pre-Lord of the Rings which he didn't write until way after he was one year old). It also means she's cute, probably. If she were ugly, she'd probably be described as "goblinesque" or "troll-like."
    Being tiny and demure would also explain why her look "disguised an intrepid spirit and unfaltering will." I hope "intrepid spirit" and "unfaltering will" are euphemisms for "horny like a goat in spring."