I would be curious to hear what you think WTM was missing that Examination Day had if you have any ideas what it was. Could help me with what "feel" to aim for.
Well,the core concept of Examination day was to prevent your students from passing your exam: easy! in WTM you have to track how many days the parents expects you to keep them and then all of a sudden they have to pass the exam, otherwise you don't get paid (i may be wrong here but i remember you have a good reason to release them). This wouldn't be bad per se but there was nothing suggesting you during the exam that a girl was "ready to pass" and the problem is that you are working hard to make them "dumber" let's say and when a girl is ready to go she is not working hard to pass your exam, she risks to fail because she doesn't complete the exam on time...
The second problem i had are the photoshoot: they are OK-ish as a game mechanic but they were too grindy: every time you have to scroll through all the photo already taken to take the new ones, i'm ok with a bit of grindiness and i'm ok with not starting right from where you stopped last time but not with going through all the photo all the times.
On top of that, when a girl passes the exam you lose all the photo taken with her... i mean, i worked hard to get those photos and to use them with the sponsors, why do you take them away? So i find myself that i started contract with more demanding sponsors and all of a sudden i have no more photos to sell to them or the girl i wanted to send has passed the exam and i can no longer fulfill the contract.
My perception was that WTM main game loop is not the exam anymore and the focus is more on those side activities, which i believe is a bit of a shame.
My very personal feeling is that it would be more enjoyable (for me) to expand on the exam mechanics itself, with rules, tools that can help you (vibrators, plugs, clamps) and other ideas (dunno, black market for panties).
The side activities are fine, but should not become the main focus as they are in WTM, because it has become a game where the focus is collecting photos from the pornstar photoshoots (and that is not very funny for my personal taste), it lacks the interactivity, the personification the cohesion with the gameloop. It reminds me a bit of the HTML type games but not the good ones.
Having said that, i'm sure that there are plenty of people that appreciated the work done in WTM, and i'm also sure that there are many ways that would turn these side activities in fun game mechanics.
What i think is the very difficult part is to find the gifs and videos for the exam actions that works well in a cohesive way and this is, from my point of view, the point where time must be spent. The photoshoots are easy to make cohesive because the photos are all from the same collection.
I'm sorry for the wall of text, and please remember, this is just my personal opinion.