How often I shop with my SA:
Don't laugh, but this week, I went almost every day (my office is near the boutique). To the point where I told the security guard "see you tomorrow" instead of just bye. Out of that, I ordered 2 things, bought 1 and got this year's card out of it too.
What does my wishlist look like:
Like a tornado went through the stockroom?

Just kidding. Currently, I have a mini Roulis, an SO Kelly combination (I was asked to think long & hard about what combo I wanted, so I have my options), some bracelets for my watch, a bunch of homeware, a dress. On the fence about a 24/24 that I saw, so it's not really on my wishlist, but I may pop in to try it.
At some point, I may add a KP (have a Cut already so I'm not in any hurry) and a mini Bolide (this one might go on my official wishlist next week). Everything else I'm looking at is in season, so it's just a question of requesting them when I feel like actually getting them (I don't want to waste my SA's search efforts if I'm then not ready to purchase).
Counting towards quota:
From what I understand of H USA, the bags count towards your next quota bag.
But remember that at H, nothing is ever guaranteed and as much as you feel it is a game, with a target $ amount to reach, that isn't the case. Even a confirmed SO could end up being canceled for a variety of reasons. What counts more is genuine enthusiasm for the brand and a great human connection with an SA/SM.
@Ball is absolutely right, and it works wonders to go quite regularly, EVERYWHERE. I'm currently in Europe and it works there, but it' worked in Asia and the US too. That's why I suggested smaller items in the beginning, as you'll want to solidify these visits with purchases. BUT, and that's key in anything Hermès, ONLY GET THINGS YOU WANT (or are planning on giving as gifts to loved ones). Don't just buy random things for the sake of tallying up "credit". An offer for BKC or SO isn't a "gift with purchase" that you end up accessing if you have enough points.
Have you considered dropping a subtle hint such as "My dream bag is (insert quite detailed SO description here)."

Honestly at this stage, a nudge-nudge-wink-wink might be in order given how good your SA has been so far.