Hi there,
As far as your own applications, essays, and school research are concerned, I strongly recommend you approach Round 2 as if Round 1 weren't even in play. As you know from your Round 1 experience, telling your story, crafting the perfect essays, getting to know programs inside and out (info sessions, visits, conversations with current students and alumni, etc.), and communicating all of that in your applications is a very involved process. If you wait too long, your applications will suffer and your Round 2 chances will be compromised.
The last thing adcoms want is to receive Round 2 applications for which the applicant likely applied elsewhere (i.e., to the schools they *really prefer*) in Round 1. And then after not getting any good Round 1 news, they cobbled together some Round 2 applications in the final weeks. That is a recipe for disappointment in both rounds, and you'll want to avoid that.
From a logistical standpoint, not knowing final outcomes until mid-December effectively prevents you from waiting to start your Round 2 applications until the very end. You can always *stop* working on applications if you get great news in mid-December, but you can't make up that lost time if you wait to start. I know that can feel like a daunting task after just completing the Round 1 applications, but I encourage you to take a break for a week or so if you need it, then re-gather your momentum and give Round 2 your best shot.
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You have a little more flexibility with recommenders. As a first step, I would definitely explain the situation to them and give them advance notice on the schools, the questions, and what might be required of them. The recommendations are generally similar enough that they shouldn't have too heavy a lift to submit the Round 2 recommendations, but you do start to run into the holiday season at that time, so you have to manage that risk.
With that mind, the rest depends on your relationship with the recommenders, how much trust you have in their ability to get this done in the last two weeks of December and first few days of January, and the number of schools to which they'll need to submit. If you have a great relationship with them, they're very diligent, and it's only a couple of schools, then you can probably wait to give them the green light (though in all cases you should discuss this plan in detail with them in advance).
But if there's more distance between you and them, you're not sure whether they'd fall off the map during the holidays, and/or it's many schools, then it's likely safer to have them go ahead and get them done no matter what. You don't want to leave anything to chance!
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Best Regards,
Greg