The JW's that I observe who are comfortable and happy to a degree are those ,like some of my relatives, who ignored the WT's advice and made sure they had all debts paid off, a nice property, and a pension.
Some of these spent many years missing meetings, and missing family life, in pursuit of this outcome, they now are in a position to Piosneer and look down on their Brethren who actually tried to "keep their life simple".
These latter still have to work at menial jobs way after retiring age to make ends meet.
The first lot may actually be more happy by ignoring the WT, the latter are finding out that listening to the WT is not the way to happiness, let alone the way to paradise.