bear88 said: "haterobics, does your ice-vein strategy of waiting until the last minute work when buying for 3?"
It depends on the show and how aggressive their premium seating holdback is. My strategy only started when tickets for a new show went on sale, and the only available regular-priced tickets were often the extreme sides and rear orchestra.
The main thing to consider is this strategy is to nail the best seats without paying premium prices. While some shows slip up and also make these seats available with a discount code, most do not. So, if you want discounts, this won't work.
Also, I live like 2ish hours outside of NYC, so my other benefit is I don't have to be concerned with when I go. If I have an open weekend, I can pop online on Thursday and Friday and if a Saturday ticket I like for a show I want to see opens up, I get in the car Saturday and drive in...
As for whether you will be able to get 3 tickets instead of singles/pairs, it will vary based on the theater's accessibility options and premium strategy. Pretend you want to buy accessible seating in advance, and see what sort of numbers they have available. Some will have two or four seats together near the stage for low vision/hearing-challenged patrons, or potentially transfer seating. Those will typically be the ones you want, as opposed to being in the last row or on the extreme sides for wheelchair seating. You can learn in advance the schedule for when a theater flips accessible seats into regular seats online by pretending to buy tickets for this week, for example. You can also ensure those seats are still available for purchase, too, since that is critical. As for premiums, it will depend on how they are configured. Shows will often have two premiums on side orchestra aisles, and far more in the center. But for three people, it will depend on how they release them when they start downconverting them. If they release the side orchestra aisles, then you'd need them to release two rows at once, to sit together(ish) with one of you sitting behind the other two. Whereas if they release 3 or more in the center, you'll be fine.
Also, keep tabs on StubHub, since those sellers may get skittish even before Telecharge/Ticketmaster and start reducing their prices.
Usually you can practice in advance and see how it going to work. But the major downside of this strategy is that you are counting on buying unsold seats. So, if a show sells all of its seats, then you're not going. Fortunately, they seem to prefer being greedier than smarter these days a lot of the time, so they really do hold out as long as possible to make extra money on premiums.
The only other thing I would say is your characterization of Gary as "its appeal lies mainly in the stars you'll never see on tour, but no one has seen it," is only its appeal now and, having attended the 24 Hour Taylor Mac concert and seeing Hir twice, Taylor is someone I'm hesitant to consider a gamble. In any case, once it starts previews, this will become a known quantity and quickly. Gary is one of the few shows I did buy advance tickets for, since they offered very few regular price seats in the second or third row on the center orchestra aisle the day tickets went on sale.