What now? - I can't see you ever having a perfect excuse to leave, even if things go "tits up" for the Society (as we say here in the UK). Any hard times that the Society goes through, even if they are legally responsible for their own misfortunes, will be spun as being an attack by Satan, or persection, or whatever. Any who leave at such a time will be branded disloyal. In the minds of indoctrinated witnesses, there is never an "honorable" time to leave.
However, even though the religious element of the organization will always be around in some form or other, I can foresee a time when the sheer scale of the cutbacks and downsizing becomes so dramatic that people start leaving en mass. Perhaps this is what you would like to see? Sometimes I wonder whether I allow over-optimism to cloud my judgment on this issue. However, as far as the cold hard facts are concerned, the Society no longer looks as invincible financially as it once did. The internet has been a real game changer in this regard - something the earlier generations of "apostates" never had at their disposal.
I keep going on about it, but last year saw an unprecedented 16% drop in the number of branches. That sort of thing would have been unheard of only a decade ago. Something is definitely going wrong for the Society financially, and a flood of Conti-inspired lawsuits will NOT help the situation at all. I don't think it's a chicken/egg situation. I see the two possible outcomes you propose as coming one after the other quite nicely. But there will always be a religious representation of the JW faith for the forseeable future, even if the Society becomes miniscule in comparison to its former glories.
Cedars