First, it had a very good run for the time period. Not as long as the biggest hits, but very good.
Second, as Sondheim has said, the biggest hits are almost always shows that tell the audience something it wants to hear, and Gypsy tells the audience something it doesn't want to hear. A show can be sort of sad or dark in some way and yet tell the audience something it wants to hear. Fiddler is a good example. The ending is sad, but it's also affirmative. It tells us that the family will endure. Gypsy, according to Sondheim (and I think he's right), tells us that eventually we must become responsible for our parents. We become the parent, and the parent becomes our child. No one wants to hear this.
Third, it was very strongly associated with Merman, and there may have been fear that it wouldn't run without her. She agreed to tour in it, and she didn't like touring, had never really done it. (A tour of Red, Hot and Blue never got past its first stop, Chicago, and I think that was the only time she even agreed to tour one of her Broadway shows.) But if they wanted her to tour, they would have to close the show because there was only so long she was going to do it. It was an exhausting role, and she didn't really like super-long runs. She was miserable during her third year in Annie Get Your Gun. In fact, Gypsy shut down for five weeks during the summer of 1960, probably because Merman really needed a vacation.
I think that a book on Ann Sothern says that Sothern (who later played it in stock) was approached to take over the role when Merman was ready to go on tour, but it didn't happen. Business had probably run down enough that bringing in a replacement would have been risky. My impression, which may not be correct, is that if Merman had been willing to play out the run on Broadway until it was no longer consistently making its weekly nut and then tour, it could have run at least a few more months. But better to get out while it was still doing pretty well. It was far more cost-effective to send it on the road with the Broadway sets and costumes and as much of the cast as wanted to go.
As for the Tonys, which were far less important then than now, if it had opened in time to be eligible for the 1959 Tonys, it would have easily been won best musical, probably would have won best actress (though Verdon might have given Merman a run for her money), and had a very good shot at winning in both featured or supporting categories, musical director and costumes. (There were no awards for best book or score in either season. And at the time there was only one director award covering both plays and musicals, and Robbins would not have won in 1959.) It also would easily have won the New York Drama Critics Circle Award for best musical.
But by the time of the Tonys, it was almost a year old. Some have said that Merman's performance had deteriorated and that's why she lost to Martin. Others have disputed that her performance had deteriorated, and have suggested that Martin won because she was playing a much more sympathetic role and was better liked personally.
And, again, it's not a show that tells people want they want to hear, and that affected it at the Tonys. Both Fiorello! and The Sound of Music do tell people things they want to hear.
So The Sound of Music got the votes of those who liked the sentimental crowdpleaser, while Fiorello! got the votes of those who were impressed by its seriousness. Gypsy was not widely viewed as a serious work of art at the time. There were some who saw it that way, but most saw it as a good musical comedy, even if a bit more serious than most and perhaps even a bit disturbing. But, still, a musical comedy.
FWIW, in the 1960 voting for the New York Drama Critics Circle Award for best musical, Fiorello! got 10 votes, Gypsy and Bye Bye Birdie each got three, The Sound of Music got two, and Greenwillow got one.
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