So we can expect without too much unjustified optimism (as probably is expecting "much" faster development in the future):
Currently/In few days or weeks: Amy + Maxine mole rat campaign.
Late 2023-early 2024: Faye
Mid-late 2024: The Twins.
Late 2024-early 2025: Liz.
Mid-late 2025: Alice.
...
All other girls: Before TES VI, probably.
With that general perspective and theoric schedule, as many of the last weeks comments have been very pessimistic and despite some previous message I wrote was mostly negative, I'm still not totally pessimistic and I like the game a lot, I consider myself a fan and it's one of the adult games I enjoyed the most but among the ones that frustrated me the most also by what I consider wasted opportunities. I think I will never be totally satisfied by it considering what patreons and probably developers tastes and preferences seem to be, very different to mine, basically my "favourite" girls got the less satisfying scenes and stories imo, but that won't stop me following the game until the end and enjoying many other parts in it because despite the frustration with "my favourites" and few other character changes, The Headmaster is full of good content as no other game with similar focus (spanking, education/manipulation, "western" school setting). Anyway for all this I want to comment what exactly I'm optimistic and pessimistic in regard The Headmaster future development.
I'm mildy to totally optimistic for the following:
- I think is almost sure this game will continue its development for at less a couple years more and I personally think will be somehow finished (how rushed and how much potential content will be finally excluded is another story), even if development last several years more, I think we can be confident that the game will continue its development.
- Hopefully Cassandra, Debbie, Amy and Priti stories will be continued or finished during those updates or some more. I think is very plausible.
- The introduction of some eventual medical examination with headmaster participation seem possible too by the introduction of a second medical scene in current/imminent update + the image previews showing the nurse (probably not what I'm expecting though...).
- A bigger amount of sex in some of the girls stories is almost guaranteed, probably also an increase in quality but hopefully at least some of it could be also outside the punishment system, even if it is just in some other special.
- Increasing corruption and lewd non-directly sexual scenes, subtle innuendos, girl initiatives, headmaster consciously triggering spicy situations, nudity and half nudity, etc all seem very possible. Maybe some temporary "cheating" over the general rules? Breaking ingame rules and sharing secrets/plots with other characters are always good inclussions in adult games imo, but I'm not so sure if Althos likes that or if he is more strict with inworld rules.
- I think Priti story probably will develop a bit more/end in a satisfactory way to most players including myself. The only girl with curvaceous body (but good/insecure girl however) with a satisfactory enough story and good scenes in which headmaster seem personally very interested in the girl is Priti. She is fun and cute in a non very annoying way for those that despise "kawaii" overdose.
- I think Faye story/development will be probably good too. I liked her small first content and Althos seems pretty consistent with the character personality/interactions.
- I hope something more with Debbie besides her role as punisher buddie. Her change was the opposite of Cassandra, way too deep and complete, she was the meanest rebellious girl and now, after some Sally punishments became some sort of obedient fascistic cop, c'mon! Even if developer decide the full lesbian route for her (which wasn't my impression by reading her dialogues with the "watching porn" topic, the headmaster blowjob and reactions, the "confidence" scenes, etc), at least I hope some temporary return of the rebellious attitude or some autority abuse as prefect with at least one headmaster personal punishment as response. I think this last is more or less possible considering Debbie precedents.
- Some good content for Alice? This is the most mildly optimistic of all examples... Almost cope. After what they did with Cassandra entire story, The Twins first scenes and punishments and Alice and Harriet full nude introduction scenes I have low hopes for any development on confident/mean girls with curves combo. I'm not sure if the problem is just patreon restrictions as other user mentioned some days ago so the only problem is the "confident/rebellious" archetype which favours "forced" approaches to punishment which is taboo in patreon apparently (which could explain also the quick transformation of Debbie from chaotic mean gal to corrupt but obedient cop archetype... to diminish "forced" content by the main character to the minimum) but I still think fanbase maybe also in the case of Althos favour good girls and small bodies content over mean girls and curvaceous bodies. However looking to the Alice preview images with a more "personally invested" headmaster + the interactions in the special events and the fact that headmaster seemed somewhat more personally interested in Alice (or her tits at least) than in other big bodies girls from the rebel group and specially the comments by Althos about Alice having a lot of fans (I think it was precisely after that 2021 poll?), all make me still mildly optimist for her... I will need to play her part before believe good stories and satisfactory scenes for curvy + mean/confident girls is possible in this game.
- Also the presence of other staff members in preview images, certain quickness in sexual interactions with some of those older characters in previous updates + whatever is doing the nurse in The Twins 0.16 pre-preview image give me some hope for action with Kate, Izzy or other staff members in the future.
What I'm pessimistic about:
- There will be not "main" girl status with proper punishment system and deeper story for Harriet, Donna, Emily, April, Charlotte, Maxine and Nina probably until 2026 or more, some of them probably not before 2028 if they are included at all.
- Ada, Arabella, Jasmine and Olivia probably will never be included in a big story/ complete punishment arch which makes more dubious their inclussion in first place, with Ada exception maybe as it seems she could have some relevant role for "main story".
- I don't expect anything good enough in the rest of Cassandra story. She always was one of my favourite girls to spank/educate precisely by how despicable she was, superficial, selfish, cruel but intelligent and also by the frequent allusion by some characters about how the girl has a big/the biggest ass (even if it's not so noticeable visually ingame) as both circunstances are greatly favourable for a spanking focused game, she was just very spankable. The character model, body, face and expressions is in my top 5 for sure which is another plus. I wanted badly to spank the girl personally via headmaster since first appareances (something that he seems to want too according his early dialogue) and to deeply change the girl attitude in a way more personal and invested route. However as I mentioned in a previous comment what we had instead is headmaster offering Cass to the other girls for the first big nude punishment and later, even worse, starting her training to "manipulate others" so she can make her dream true: To be a professional gold digger... Punishment have been good so far, but the terrible blowjobs scenes are a bit off. Among my personal sexual disappointments in real life I can't count a "sad blowjob", I don't even knew those things could exist at all, every blowjob was a happy and nice event according my experience. I should thank Altos for so educative content...
I think it's possible that Altos will offer some plot twist at the end for Cassandra with a machiavelic headmaster manipulating the girl to accept a true education and really changing her attitude and life aspirations, but even in that plot twist scenario the rest of the experience will be not really enjoyable to me. She was just perfect for the classic punishment/education route not for headmaster helping her to become more powerful without changing the core of her problems in exchange for bad sex and apparently giving it up with her education. In videogames the path and the experience "during" is always more relevant than the result.
- The girl I'm personally the most frustrated with is Harriet and I hope even less good content from her than from Cass despite her story is supposedly much less advanced yet. Harriet was among the most atractive girls to me since start despite the very limited content at first, with some additional precocious "apparent" confidence and independence that makes the spanking/education route more interesting and a really nice body and face with an attractive gaze (despite the game general artstyle limits a lot characters personalization it was one of my favourite models, probably the absolute first), but the girl suffered the worst first nudity/introduction to punishment scenes in the game by far imo... Comparable to Cassandra gang-spank but much worse as Cass was a hateful person at that point which could justify headmaster disdain/contradiction with his own thoughts ("I want to punish you personally" thing) but in Harriet case there is nothing that justify headmaster attitude, just pure lack of interest in Harriet? After the few promising body searchs and the entire investigation... we have only that anticlimatic thing? If we add to the uninvested intro the fact developers won't probably touch much of Harriet story until 2026 or more... if they return to her at all, well there is not much to be hopeful here.
- The Twins. Again one of the my favourite girls to spank by personality and models (the biggest pranksters, confident, redheads, nice body) but once more I'm pessimistic about their evolution. I think Althos will probably do a better and more satisfactory (to me at least) job with Mary and Louise than with Cass or Harriet and they are also part of a much closer in time (probable) update. However I seriously doubt developers will add enough individuality as they insist in the non-solo mandatory double punishment (why always shared by both twins and mostly by two punishers?). I like them as twins but I would prefer a specific story, personality and punishment evolution (even if shorter) for each girl. Still I know I will enjoy their updates no matter how Altos decide to develop them, because their problem isn't as relevant as in Harriet and Cassandra cases.