The game is least forgiving in the first few days, after that, it really opens out into people remembering the choices you've made in the game. Even if you've still been making bad choices, it's pretty fun from there.
I too am taking advantage of the summer sale and am about 20 hours in and still wildly infatuated with this weird, weird amazing game.
After a while you start getting a slightly better idea of what's going on, but that doesn't make it more "game like" if anything, the more you learn about the game, the more it reveals itself to be a giant tool to explore meta-narratives and there are some moments of conversation regarding this that are absolutely chilling.
He was unpopular at school; hung out with the lower classes; used cocaine; once shot the letters 'V R' into his living room wall; was a member of a club where no member was supposed to speak to another; only survived as long as he did because his brother was a major government official.
It's true that Doyle never mentioned it, but it's logical that Holmes would want a place he could duck into for a quick meal; or a nap; or to put on a new disguise. Watson does say that Holmes had bolt holes around London, so it would have been foolish for him not to have a membership.
I remember reading about his membership in a non canon work.
If you're a fan look up 'The 7% Solution.' It's available as a novel and a movie; Holmes meets the only doctor capable of curing his cocaine addiction, Sigmund Freud.
Ah yes, this was my exact experience as well. Then I restarted and leaned into being a drug-fueled maniac superstar detective who may have dabbled lightly in communism and completely crushed solving the case.
Columbo is all four corners at once. He always looks like he's doing rough, but he never quite looks like he's falling apart. He's just happy where he is. And he does use vibes in addition to algorithmic logic. He usually knows who the murderer is after his first time meeting them. He just has to prove it using the proper rigour