I'm at the point where the dude at the Lake is supposed to find the keys, but he never does. (It suggests I talk to MsNewman, but there's nothing new there either), Please Help me, after spy Silly at Monday afternoon twice but still not working
This is (as far as I know) always a user thing. I have pushed one thread or another on play-throughs in less than clever directions, and there are breaks there (mostly because putting them in voting order can cause issues, though I think only the no-choice-but-after-school Cassandra one remains) but generally speaking, the triggers in this game are way more solid than anyone should expect from a vote-to-develop game.
On this particular one, you have blown off better help than I can provide already. I'd suggest following the advice you already received.