Regarding the problems people have,
I personally had nearly no problems. I use windows 10, english, with japanese locale (natively set as I was learning japanese when I set up this machine), and I set the timezone to japanwhen starting the game. But after an hour, to stop irritating flux, I reset the timezone. Only once after did I get a problem where the training scene locked up, and I could fix that by just reloading and starting it again.
I could also train the third princess by just massaging her breasts - just seems important to stick with what you start with.
I only went to insertion in the third session.