My biggest concern is the Watchtower and it's authority
Yes, that needs to be your biggest concern.
Having been raised in and lived the life for 42 years under their authority, believe me, I can be trusted to know what goes on. If I could talk to you in person, you could see and hear my sincerity for your plight. My son is your age and I wouldn't wish this situation on him for anything. If I believed in angels, he would be one, for being the one that brought us all out of JW's three years ago.
I wasn't allowed to be in contact with any "worldly" boyfriend either during my years as a JW growing up. I was followed, spied on, reported on to the elders by my own sister for continuing to see my non JW boyfriend, and suffered from a public announcement of punishment in the congregation. Yet, I stuck around......for 30 more years. Brainwashed.
The authority of which you speak in your above comment, will RULE your life and destroy your true self, eventually. If you had seen your father, as I did mine, literally surrounded by the Watchtower's literature before taking his life - always seeking to allow this authority to rule his life, searching for THEIR answers, maybe the depth of what is involved could be understood.
For now though, this is a lot of info to digest, and you need to experience more life, before you give that life over to an organization (cult) like JW's.
I would suggest you get a copy of the book by Steven Hassan, "Combatting Cult Mind Control" and read it while you still have somewhat of an open mind. Perhaps you can share it with Jon and get his viewpoint on it's contents. Sadly, it's another thing he won't be allowed to do though, read this book, unless he does it on the sly and feels guilty for doing so.
All the best to you
(now the count is up to 14, 478 views, hmmmm....)