I've been thinking about adding dreams as it is frequently suggest, but I don't want to bloat the nights too much either. Maybe it'll be experimented in the next few updates, just get the feel for it. There is already progression events, so dreams could work in a similar manner. The problem with changing texts that say exactly what the player needs lead to a lot of "how do I unlock X?" questions. Some things are just a little vague and I get bug reports because of them (lead exemple being the final event of the training). I do like the idea in terms of immersion, that's for sure, but it's the trade-off with gameplay requirements.
Thanks for even considering it! I like sandbox games even if it's hard to balance that gameplay, between complete freedom and a more "immersive" background story (or stories) that give you context, without railroading you.
I personally don't have any qualms about "handholding" in-game quest tips - if anything, they sometimes provide me with an excuse to let the MC make choices I wouldn't personally make, without having to make assumptions about the MC's background.
Hey, this is just another quick idea that you probably already thought about, it might be cool to have an email client in the PC and create a penpal NPC, an old school friend that the PC can sometimes exchange mails with and tells us about their own journey of self-discovery, allowing the PC to respond in different ways. I think of the crossdresser friend in TSGE as an example of a supportive character.
But maybe this would be redundant, if Crystal would get a bigger role as a friend and confidante, who unlike Kara wouldn't be pushing the MC forward, but rather giving moral support. I feel that Crystal's role transitions quickly from a leading one to a background, repeatable event and hope there's more in the plans for her.
That reminds me of event with the girl you can fuck in the college café, that becomes a dick you can suck when you advance enough in your crossdressing. Isn't that part of the progression events you mentioned? Sounds fun if she had a name and acknowledge your progress, such as when you transition to sucking dicks, it's the same girl that acknowledges your change and suggests joining her instead of fucking. You could even make it an option (fuck the girl as before or suck cock with her), allowing the player to roleplay different rates of acceptance or reluctance.
Sorry for another long one! Got carried away. Thanks again and good luck!