Just to answer the questions you pose at the end such as does it make me sad? With regard to my parents saddens me to see unwaivering loyalty to such an uncaring group and even worse that they have so litre self esteem they can't see it. For example even in very poor health and inclement weather they still 'cart' or attend meetings late at night. With online stuff there is no excuse too big or talk too small to miss. I've rarely seen people round offering to help. I see wasted lives, my parents aren't drones they are quite odd ball and very middle class I suspect the only reason they haven't been pulled up for fraternizing with us is that they give handsomely to the Borg although I have no evidence of this. We do family ccassionally have spiritual ding dongs but I've found these counter productive its better to show love and when praised for our kindness I drop in stuff like- ' I don't think you're used to this' or ' that's what Christians do" and just shrug not making a big thing of it.
My sibling on the other hand had woken up and started to fade, he then married a devout JW and has been awful ever since, they virtually shun us. We did have a close relationship for many years but that's just gone. This makes me feel sad angry and frustrated i cannot see how he cannot see but i suspect he isnt in it for the belief but because his Mrs makes him toe the line. Her family are very presurizing so i see him as weak.
The only other issue with trying to wake someone up is it reveals to them just how apostate your views really are. If as in sibling and in law they return they have even more ammo to use against you and shun you.