I try my utmost best to prevent cases like that, especially if you're very much ahead and only follow certain characters things can get a bit wonky at times, and that's only because I'm not aware of it as there are over 20 hours of gameplay and like 400 events or so.
Stacy is very easy to meet so it's a bit strange you haven't met her yet as she's there every day. It could be that Eva's there in the morning while talking about certain things, including the auction, I've changed that a tad.
From now on she'll only talk about the auction if it happened, though it shows you're way ahead because she only mentions it after day 80 while the auction is at day 50. Normally by now, you should have unlocked part three of the game which is where things get VERY interesting if I say so myself for many different reasons.
As for Gary, that's a very nice find and I've fixed that straight away, thanks a lot.
Glad you're enjoying the game so far. It's a rake-to-riches kind of story that get's better, larger, and more interesting the more one plays as is by design. Not only that, we've upped our game design skills a lot so by the time you reached the middle of the difference is absolutely noticeable.
That's very late for sure as normally he shows up on day 68 but there are two triggers needed which are
It's not possible for it to get bugged. All good though, nothing wrong with loading an old save since there are lots of things that unlock after meeting 'The Boss'.
I keep a close eye on players getting stuck at certain points and make changes accordingly. It's planned for the new major update to have a very detailed journal which will probably always be 100% on point thanks to Master of Puppets who is helping me out with that one.