JoeW4 said: "Recommending Off-Broadway this far in advance is tricky because most of what will be playing has not yet started performances. But here's what's on my radar (loosely in order of how I'd prioritize them, personally)
If you're going for buzz over ease, you could try for Hell's Kitchen, Walk on Through, or Danny and the Deep Blue Sea - all of which are hot tickets, but there's always lottery or cancellation lines, if you're willing to spend the time/money. Similarly, Here We Are will still be playing - not too difficult to get a ticket, but maybe difficult to get an affordable one.
Rachel Bloom is bringing her one-woman-show back for a return engagement at the Orpheum. I saw it and really enjoyed it.
The new musical Buena Vista Social Club will also be playing at Atlantic
Spain at 2nd Stage, and Manahatta at the Public are both new plays, currently slated through 12/17 only. So depending on when your open slots are, you might be able to squeeze one in. And you could keep your eyes out for extensions, if they end up being warranted.
There's a revival of Tennessee Williams' Night of the Iguana with a strong-looking cast, playing at Signature (a rental, not produced by them).
The new Lachiusa musical, Gardens of Anuncia is currently playing at LCT through the end of December.
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Thanks so much for your thorough response! I already have tickets for Gardens of Anuncia, Hell's Kitchen, and Here We Are; I'll check out the other suggestions you've made. :)