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 "Going off my trolley. And you're trying to help me get back to the way most people live, 's that it?"

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"Going off my trolley"
This means going mad. So this is another interpretation of what's happening to Lew. Has he simply gone insane? In a way, can't that be seen as losing one's path to their destiny? If we assume madness as some kind of outside affliction, couldn't it be seen as the cause of derailing so many people's destinies, causing them to miss out on the life they were supposed to lead had they kept their sanity? This is a philosophical argument because we can just as easily believe that insanity was their destiny and there was no way to avoid it.
    In Mason & Dixon, Reverend Cherrycoke is banished from England after being declared insane to rebuke him for his leaflets proclaiming certain personages in authority as criminals and miscreants. Being declared mad is a punishment for not keeping your trolley on the track expected of you. Cherrycoke realizes that his name, the thing that is almost interchangeable with his actual identity, never belonged to him. Names are labels for bureaucratic use by authoritarians to keep watch on and to punish those who bounce from their intended rails. Lew is suffering much the same problem. Lew doesn't remember sinning but he's paying the price for somebody using his name (presumably him but, well, he doesn't remember it) which is now tied to the horrible reputation. His name is the signifier for others to treat him punitively.
    I suppose Tyrone Slothrop also goes mad in quite a number of ways in Gravity's Rainbow but I can't quite pluck out any specific scenes from my memory right now. But as for names, he does, in a relatively close space to the center of the book, become dubbed Rocketman. With his new name, he accomplishes things Slothrop probably wouldn't have had the nerve to accomplish and finds himself in places he almost certainly would never have found himself as Slothrop. Like a rocket blasting free from Earth's gravitational pull, Slothrop frees himself by shedding the name that doesn't actually belong to him and taking up an anonymous superhero moniker.

"you're trying to help me get back to the way most people live"
I don't know if Drave is trying to do that, exactly. At this point, I'm not sure what Drave's interest in Lew is. Unless Drave is the devil and he's trying to grab up another soul. Otherwise what does Drave have to gain in this matter? Unless this is some kind of Scientology scheme and he's trying to get Dave back out in the real world to become a success and to owe that success to Drave's weird community, kicking back monthly payments to Drave.

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 Somehow this got back to Drave, who, deeply though perhaps unhealthily amused, struck Lew repeatedly with a "remembrance stick."

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I meant to read Dianetics in my thirties but never got around to it. I'm sorry that I didn't because I think knowledge of Scientology would come in handy while reading this chapter. The link between this weird self-help commune and Alcoholics Anonymous sort of unravels when one of the leaders begins hitting a new recruit with a stick to help him remember. Unless the remembrance stick is just a metaphor for some grizzled old timer taking you out in the dark church parking lot after the meeting to drink one more cup of coffee and to share a cigarette as he acts like your new best friend and encourages you to keep coming back. To him, he probably thinks he's being friendly. To the newbie, he's definitely up to something and that something might be sexual and maybe another beer wouldn't be a bad idea.

The remembrance stick just sounds like some weird ritual that Scientology would be into. I also wouldn't be surprised if Mormons had remembrance sticks. Come to think of it, I also wouldn't be shocked if half a dozen different Christian denominations had them.

I get being beaten with a remembrance stick. You've got to remember stuff! But being beaten with the remembrance stick when you haven't forgotten anything at all just seems out of line! Hershel didn't simply not tell Lew where he would be; Hershel aggressively didn't tell Lew where he would be! They set Lew up for failure. That also sounds like a method of brainwashing people used by Scientology!

"Drave" and Hershel
It's weird that these guys have no last names and their first names are slightly misspelled, right?

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 Hershel was large for one of his calling, looking less like a uniformed jockey than an ex-pugilist.

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Hershel is security. He's there to keep people from leaving. This is a cult and perhaps I was naïve to think it was an analogy of religion or Alcoholics Anonymous. I'm beginning to suspect this is an analogy of Scientology.