Kat's plan is either a) keep her job, ideally while gaining more liberty to run things as she pleases, or b) ensure her legacy in the club. She knows Hana is morally/ethically against the club, but since August has named her as his heir, Kat needs to ensure that 1st) Hana doesn't shut down the club completely, 2nd) Hana doesn't stop the Carnations Competition, and if possible 3) grant Kat more leeway than she ever had under August and Chuck. She also takes every opportunity and uses every strategy afforded to her, so if Edwin offers an opportunity to sway Hana toward her goals, Kat won't hesitate.I think any of kats plans regarding going against chuck and august would have been around before edwin joined the club and her plan involved knowing that hana would think Edwin is "attractive" (either "hot" or "attractive/good" enough to stake her entire future in a very very illegal business would be a pretty insane plan especially considering you can lower Hana's affection and raise her anger which seems like a risk kath would want to avoid (giving hana more reason to dislike the club)
Has there been anything in story showing that Chuck would want to give Ian his shares (beyond chuck being a family first guy)? Hana "needs" the money both in the short and long term and august even mentions something about him reflecting on his life recently to Edwin whereas chuck is as reflective as a slab of wet concrete, also Ian is not a guarantee at the club (in the future) either since he has the possibility to be more introspective in the recent updates.
iirc there will be two "paths" that endings will branch off from either Edwin wanting to stay as part of the club or Edwin attempting to leave it so both/either your proposed endings could happen
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Both August and Chuck are actually self-reflective, but since their lives have (allegedly) taken different paths, they've come to different conclusions. August sees that he's done so little good that he must recompense for all his evils, while Chuck realizes that he has so little time left to state his lusts, rather than spreading out that enjoyment across a lifetime (which he regrets). Although Chuck's death is likely closer than August's, the mobster's guilt presses him to be more zealous in paying off his debt than Chuck's "eat, drink, and be horny, for tomorrow I literally will die." So if both men are looking at their final moments, and August has already been making moves, Chuck is definitely thinking about his place in the club, and what his death would mean, but naturally this isn't something he would advertise, or open up about until the only correct moment (which may be the reading of his will). The other reason not to name his heir yet is because it's uncertain. Like you said: neither Ian's nor Edwin's long-term futures with the club seem certain, and not because they will be fired, but because neither yet seem interested/motivated to make the club a permanent feature in their lives. Ian certainly matches Chuck's current hedonism, but he lacks any drive beyond that, so not exactly apt to inherit a third of the management/administration of the club. Edwin reminds Chuck a lot of his younger self, especially the drive to become a doctor, thus he does share his regrets of not embracing this perverted side of him when he was full of youthful energy and vigor, to direct Edwin not to make the same mistake. However, Victoria's history causes concern over Edwin's psychology, and what he would do were he given "the keys to the kingdom"; plus Chuck's no doubt concerned about Kat influencing the young man, so naming him heir is not a given either.
Yes, I agree that it's not a given that Hana-Ian-Edwin will become the new management. Kat doesn't strike me as willing to retire any time soon, and Edwin is more of a future ally to her, an additional voice to let Kat run things her way, rather than a dynastic successor. August is guaranteed to be handing over his power, position, and investment to Hana. Chuck indeed has made no inferences to his inheritance, but he has clearly shown that he has been thinking about his inevitable demise, thus leading to fan speculation over what his plan/goal is post-mortem. Although TD is nowhere near as heavy-handed as Tess in "Karlssons Gambit", there have been a few hypothetical musings about what Edwin would do if he were in charge (like effectively confessing to Dahlia in the sauna that he would have better protections for the house girls), so TD is inferring this to be a possible player-choice future. Whether Ian is the third executive, or takes over if Edwin/player walks away, or is not involved at all, or if these are each player-dependent, is known only to TD and GIL at this point.