Before I start with my answer, I remembered a tiny detail: shouldn't the coastguard/masseur's name be Adrian, and not Adrain?
Impossible. I never overthink things. Overthinking is a myth created by those who fear the true power of thoroughness...
The money is not the issue. It's the portrayal of the co-worker.
About the money:
I am not complaining about having 2,000G, nor am I saying it should be improved to pay the tuition fees. While I agree it could maybe be a little bit less flowing, this is clearly not the kind of game where one wants to have to grind to get enough money to continue the story (also, I'm probably to blame for how much I have, notably because I missed the flyer job and did not want to start a third time just to synchronise it with the other jobs).
And while the tuition "blackmail" is quite cliché, let's be honest: we are not playing
Coming of Age for its perfectly realistic portrayal of the corruption of a young woman...
So, this is an obvious plot to move the story forward and I'm perfectly fine with it (after all, I did suggest that you use it to introduce the strip-tease job). I don't complain about it. I just said that the only reason the café job
could be considered a necessity for May would be if she had to get a loan to pay for her tuition, which is not a thing in the game, and actually should not become one (since it would remove the pseudo-blackmail story thread).
As a consequence, the café job is optional for our character, while the other waitress appears to actually need it to live decently, which is why I would prefer for her character to be either less desperate / more greedy, or to have some interactions to help her allowing us (or perhaps only me) to feel we are not stealing money from the needy whereas we ourselves are actually pretty well-off (or using this money for really superficial things).
And I actually would prefer the second option, since it would portray May as less self-centered and her corruption less destructive.
I can understand the "too many lesbian scenes". I disagree with the notion there could actually be too much of them, but it's true that May's sexual experiences are greatly unbalanced in favor of lesbianism.
In that case, I refer you to my suggestion about the clothes shop job, which would lead to the waitress disappearing from the picture while still dealing with the issue of her money trouble.
As an alternative to the clothes shop job, she could also have a discussion with May leading to her creating her own webcam channel. She would thus earn money while being completely independant from May, allowing you here again to remove her as a recurring female characters, when you have already quite a lot to manage (and doing so while closing a storyline, not letting it frustratingly dangling).
In fact, the webcam show, now that I think about it, could even allow you some parallel scenes similar to the cheerleader ones (but with more freedom), which would be a bonus for you to change pace when you are tired of dealing with May's sexual antics. For example, she may include a guy (or two... why not the café's customers) in her show, and May, learning about it, would log in to watch it: still no interaction, and you could add any kind of scene that fancies you at the time without having to look for a deep in-story explanation: what would lead to her having sex with two men, or one man and one woman—or a unicorn/pony—would not matter, contrary to May (damn, I just had the thought of her spicing her show by fucking a pony with a visibly fake horn on his head, while being dressed as an elven princess—she even has the too-thin silhouette for that).
