I am reading this and it is something that we cannot even agree on whether they short of money or not, let alone why they would be short (or not).
Watchtower was clearly a giant publishing company that made humongous best-sellers that nobody ever really heard of. They sold the books and magazines and whatnot to Joe Publisher. In the past, Joe Publisher also sold the stuff to the public. That was Watchtower's main source of money for decades upon decades.
Members did not really contribute much money beyond buying the books. Oh, they kept the lights on at the local Kingdom Hall and put their modest contribution in at the assemblies and conventions enough for Watchtower to make a profit there. But the real money was in literature. Your average member gave them TIME, not MONEY. That is the model that members were used to.
The money train for literature ended quickly. When members were to donate and not buy the literature, they felt they were giving TIME, not so much MONEY. "Jehovah knows I don't have boatloads of money." And real growth of the organization has been stagnant with mostly kids of members joining. The old folks that are still around still think "TIME, not MONEY." Meanwhile, younger lifelong members are seeing less income from not going to college, they are seeing Watchtower demand too much and they are just not giving it.
Sure, they drop their money in the box. But what they used to drop in the box was a modest amount at the Hall, and a modest amount at the Circuit Assembly, and a modest amount at the Convention. Now, they see Watchtower saying various things about needing so much money and they take money they would have dropped in one box and drop it in the other. When the local congregation needs to pay bills, they drop it in there. But they just don't have more/more/more for the assemblies and conventions. And they figure Watchtower is getting it anyway from the Kingdom Hall, so they don't drop it in.
Selling properties is a crisis management solution, not a viable way to get out of trouble.