Hi Tenacious,
I'm a newbie here myself and disassociated since the late 80s or thereabouts. That is disassociated as in wrote a letter telling them I was out and wanted nothing more to do with them. I had been a full time pioneer ( that was 100 hours a month ) and a Ministerial Servant.
I'm sure many others will have their own answers so here are mine:
1. Why does the organization punish those with sincere questions when they are not satisfied with the typical "we don't know but wait on Jehovah."
To control thinking. That's about it. I once asked a question during a Watchtower study that was in no way contentious and promptly shot down in flames for having the temerity to question an elder. No one spoke to me after the meeting either which might give you some indication of how strong this view is.
2. Why does the organization feel the need to announce from the platform when someone is pioneering? Prominence?
No. In fairness it was all about encouraging others to do the same and/or give support. I pioneered in the 70s and supported myself financially by working part-time. There was an open invitation from just about everyone to stop-by for lunch if I happened to be working in the area. Equally an invitation to join me in the work.
3. Why is information a privilege and not freely available to all members such as being able to sit-in on the CO's special meeting with the pioneers?
Not sure it was about privileged information. I certainly learned nothing new at those meetings. Pioneering was hard work. It wasn't uncommon to do five-hours straight going from door-to-door alone. Bear in mind that in most cases you don't get much beyond two or three sentences of your introduction which was frustrating and discouraging. The meeting with the CO was about overcoming that discouragement and working on new introductions.
4. Why has the society not apologized once for mistakes that obviously ruined and killed so many of their members?
The Society runs on a good business model ( I mean in a bad way ). You cant sue them for accidents when using their products. And, as a magazine article pointed out, they never made a mistake. Going toward the light of god was like a boat tacking against the wind: You go sideways a lot but the general direction is forward. Nonsense of course but an easy-sell when dealing with people who want to believe. Besides, if they ever did apologise then they would never see the end of the lawsuits.
5. Why does the society fear higher education? Critical thinking and reasoning skills being developed perhaps?
That's about right. I got married and went on to study electronics. I ended up teaching at university. You could say I got full exposure to 'Satan's dark philosophies' though to this day feel no inclination to dance naked around a rock under a full moon. Ogle some of the girls on campus? Guilty as charged.
Nothing I learned in electronics contradicted what the Bible says. Ditto, computer studies, statistical analysis or systems analysis. Satan's wily ways must have got his ideas in somehow I guess. I might have made it as a doctor or in chemistry but I was already too old.
Now the caveat: Some of the brothers were also super people and good supportive friends. I think of them with fondness to this day. My mother tells me that some still ask after me so I don't doubt the love was genuine.
The 'society' on the other hand might have started out as an 'instrument of god in the execution of his works' but has become a living thing in its own right. It is a business and a business for profit which is what businesses are for.
Thats my take on things. Hope it helps. Bear in mind that my experience may not be representitive of others, less so my views.