I've generally been able to trigger him by talking to him enough to raise my relationship then by going to the sports section in the community center. When I leave the sports section he comes up to you and asks for a date.
There's no cheat code to jump to the sexvents. You simply need to raise your relationship with him (best option is via cheat menu) and tease him for a while, then talk with him and then you should get an option to seduce him.
Yeah happened in my game too; she's lost her virginity a few times now, seems to grow back. Game seems to have a hard time keeping track of birth control implants too.
1) Yes the starts are by year of the game. School girl start is in 2016, city starts in 2017, so everything will be open to the school girl.
The game is good and very in-depth, but I have to wonder: who will play through all 4 years of university with the current levels of micromanagement? The one school year is hard enough to get through and grows stale after the first few months. How is anyone going to get through 4 years, just to start exploring the post-university content? Say someone plays the game every day and manages to get through 5 in-game days per session: That's 292 real life days till you get the degree. Isn't that kind of excessive?
I’ve been playing Girl Life for two years now. I’m still discovering new paths, that’s just crazy! This game is amazing. In those two years I’ve made it around 5 times through the school year (the city start is less interesting), and up to half the university’s 1st year. It will be challenging to write enough content for 4 years university, indeed. But the pleasure to play the game is exactly there: grow with your Sveta, make her do things you never would rl and discover what happens. No need to find an timed “end” to the game. But indeed, I’d try to close some paths, which are now open end and from some point repetitive, like the hypnosis path, the Dimka path, the BDSM Mansion path, the gas station abduction path, the Dimitry path, and so on. Would be fun to have those ends being available.
Well I posted a long detailed post but then the site decided to update and eat the post, so this is a much shorter answer.
That is old imported content and if I recall correct that is where it ends, eventually it will be expanded.
10x for the very quick reply. I wish all of the quests would have an "end of current content" disclaimer
I spent two days trying to reload in case I did something wrong or advance time in case something finally shows up. 
