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No problemo my friend. The best thing to do when stuck is ask for help.

You should have discipline higher than 20 when u open the lake or else grades drop everyday.  And I don't think you get the option for Jimmy to show you until after you have had the 3rd dream. The 3rd dream happens after you speak to Ruth about the old HM's  locked journal entry on the comp. If you haven't gotten the locked entry unlocked yet it happens after Miss Chang shrinks Sally and they fight.  Miss Chang loses hilariously but still gives you the password which unlocks the entry.  Yes you have to speak to Jimmy on any weekday cuz on weekends he is passed out drunk. But once you have spoken to him about showing you  the next weekday that you visit him he will take you.

To open the safe you have to find the old HM's wallet. To do so you have to open lake access, at the Friday meeting, and then talk to the groundskeeper. He will eventually offer to show you the area where they found the old HM and that's where you get the wallet. Inside is the safe combo. Inside the safe is blackmail material to use against Ruth which is how you advance her story.

It may be bugged for you I don't know. After refusing her the final time the next day you automatically have her come after school for a private punishment. I would say don't automatically skip through days if you were and maybe don't have any other girls come after school for punishments and maybe that will trigger it for you? On my playthrough  it would have fallen on a friday but cuz of the board meeting it didn't happen til monday. Also you won't get the option to summon her after school until after you've completed this and assigned her the role of test subject.  So if you have the option to summon her but are still getting the chastity panties scenes it sounds like a definite bug. In that case hopefully you have a save game point from before this path that you can revert to and try again without having to play from beginning?

To progress in Amy's path she has to go the full weeks time without any gratification whatsoever. So the first time she shows up just wanting a release then each day she starts offering things like HJ or BJ and then offers sex and so on. If you accept  at any point cuz you want to view the scene then the 7 day counter starts all over. But if you hold out and refuse her each time on the next weekday morning after the full time period you will finally punish her and have anal sex with her.  She will then agree to be your test training subject for others to practice on.  That will happen in future updates apparently. But for now after she agrees you can summon her after school and repeat the punishments on her.  There is only one more thing you can do with her in the current version after she agrees to be test subject.  Once the swimming pool is built on tuesday mornings you can follow her into the girls locker room and have vag or anal sex with her.