Would you try to inform them of the failings of their religion if you were given the opportunity?
By the same exact token, how many people in real life look forward to the exact same scenario you describe, but in "christendom?" I have personally witnessed many such things as you describe, outside the JWs and their church members were doing all they could for them.
Yet, isn't it the JWs that will go to their door and tell them the failings of the religion that is bringing them comfort? Why yes, it is.
The one thing I have come to absolutely hate in religion is their bottomless pit of negative resources to spew against each other.
However, allow me to point out a few things you forgot to mention with your hypothetical situations.
1. A 75 year old that has been in the org for 40 years is probably beyond helping. They have been used and abused for all that time and have come to look forward to it. But, since God reads hearts and man doesn't, their fate is in his hands as to they receive resurrection or not.
2. A home bound cripple would be expected to at least "phone witness" as much as possible. The pressure would be there to get in the hours and witness any way possible. After all, the ragazines have numerous accounts of people worse off doing more.
3. The former hooker may have less abuse than she did when on the streets, but there would also be the pressure to get out more and pioneer. Her sex starved JW hubby just might sense that he is missing what she used to sell on the streets and pressure her there. Old biddies that sit in the back of the KH every Sunday just to gossip about sister so and so would most likely never let her forget that she was once once a hooker (to be fair, all religions have an abundance of these old gossip biddies). With pressure coming from all sides and then being told how to properly raise her children by a group of spiritually unqualified brothers, who cannot even agree amongst themselves, just might be somehting that could turn her back onto the streets.
All hypothetical, you understand!
So, are those three individuals really better off? If the situation described is so calming and good, why do the JWs try to pry people in the same exact situation, with the same exact calming effect you describe, away from their religions?????
If God's Spirit is filling a Kingdom Hall, how is it that Satan can manuever the ones within that Kingdom Hall at the same time?