Man proposes, and then systems interfere in all sorts of sordid ways for the pleasure of invisible observers. Clearly Jack planned on passing through without attracting any attention, but that was no longer possible.
As circumstances changed, he had to adapt accordingly. After entering the Midnight Inn, Jack altered his plans. He allowed his crew to disembark the Jolly Rancher, which had been shrunk to a reasonable size upon entering the Inn.
Those who wanted to explore did that. Those that wanted to return home did that, and others got the opportunity to rest. Jack, meanwhile, disappeared from public view. For all intents and purposes, the Midnight Inn was operating normally, and nothing seemed to have gone awry.
The nearly two decades Lex had spent in the Land of a Hundred Rivers, and then the subsequent years in the Upper Battlefield accounted for only a few months in the Dream realm. Every second of that was perilous.
