I think the overwhelming problem with trying to wake up friends and family is they have nowhere else to go. I mean these people all their friends are JWs a lot of them their family is JWs. If they wake up or agree with you in anyway they know instantly that they loose all this, many will even loose jobs.
I think there is a lot of mentally out JWs that go to meeting and service but are really just going through the motions knowing they have no other options.
Proof of this maybe one of the last meetings I went to. I was returning to my seat during a watchtower study and got a good look at how many people didn’t have their watchtowers marked it was almost every one of them. could be only about 10% are truly believers and the rest are in some way not awake but just indifferent knowing they have no other options?