It never made any sense to me at all as a born in. I've always loved history as well, and one thing the dubs always try to pull on unsuspecting potential converts is the ol':
"Can you think of a time with more wars, violence, immorality, food shortages, and disease? Just think of the two World Wars, the threat of nuclear war, the starving kids in Africa, crime, and the AIDS epidemic!"
Convert: "Why, no! Things are really bad these days. Whatever happened to the good old days?"
JW: Exactly. You see, we are living in the last days! The Bible foretold that we would see all these things in Matt 24! blah blah blah"
Even as a child, when they asked that question at meetings my mind would often drift to pages of history books as I began to count off in my head all of the other periods in history when the majority of the things discussed were far worse and more prevalent than our time.
The 1914 doctrine never made much sense to me, but as a born in, the thought of questioning the FDS was unthinkable. I knew that however confusing and convoluted it might be, it had to be true, because the FDS said so! So, I would dismiss the doubts and instead focus my energies on memorizing and being able to recite all of the dogma to the best of my ability. Most of the other JW youth had no clue what 1914 was. As a matter of fact, I bet if you were to do a survey of 15-21 year old JWs, the majority of respondents would have no clue what 1914 is supposed to represent.
It wasn't until I was about 16 or 17 when questions about 1914 became harder and harder to supress.