JW. org no longer foots the bill for most of their medical needs. Additionally, since TM3 is a veteran he also has VA benefits I am sure.
We had a special pioneer couple in our congregation "X" years ago. They were booted out of Bethel in their 50's like hundreds of others.
They had a slightly different path to Bethel service, they joined when in their 30's so they had 10+ years of work history as employees in the USA, which qualified them for Social Security retirement benefits.
In the USA, your Social Security "normal" retirement age is somewhere between ages 65 - 67, depending on your year of birth. You can elect to receive reduced benefits as early as age 62.
When the husband was about to reach age 62, he was informed by Bethel that he must begin his Social Security benefits at age 62, no option, end of discussion. AND his monthly stipend from the WTS (at the time I think it was something like $600 per month) would be reduced in accord with whatever SS paid him. If he got $500 per month from SS, his money from the WTS would be reduced to $100. If his SS payments exceeded $600 per month (not that hard to do, even with only 10-12 years of work experience), the WTS turned off the money spigot.
It might have been nice for the couple to wait until later, to get higher retirement benefits at a later age, but they had 0 option (if they wanted to remain special pioneers, anyway).
The WTS will never pay out a farthing more that they have to.