Sorry I came late to this party but I just wanted to drop my two cents....
like most things, it is hard to generalize. Even though most born-in JWs do have some common experience, their individual situations and circumstances and their own reaction and development out of these are so unique that one JW's experience can differ significantly from another's.
The largest factor involved seems to obviously be the PARENT(s) and both their own manifestation of the JW life together with their own personal baggage (which is of course intertwined). If a JW child had strict JW parents, it is likely their experience sucked in many ways - though even then any deprivations like missing Christmas or getting birthday presents is not much different then children of other circumstances that also underwent such deprivations but for different reasons (e.g. Muslims, Jews, the impoverished, etc.)
On the other hand, if the JW parents were less strict or even liberal then the JW child's upbringing was probably closer to the norm.
The second largest factor is probably whether there were any JW peers or not. To the extent that the JW child had non-JW friends and peers either because there were few JW peers of the same age or because the parents allowed them to associate with non-JWs, then their experience was probably closer to the norm.
To answer your personal question personally, even though my parents were long-time Witnesses and my father was the presiding overseer and big elder while growing up, I was able to participate in sports, school activities, extracurriculars, prom, homecoming, etc. and had non-JW friends almost exclusively. I was also not pressured to participate in field service and in fact never went out (except as a small child with my mother a few times) as a child or a teen. We didn't celebrate any holidays, nor like some Witnesses, did we even skirt around "officially" celebrating anything, except for perhaps going to watch the local fireworks show on the Fourth of July -- so that part of growing up sucked I suppose. Leaving school early during the holiday celebrations, turning down Barbara Baker's birthday invitation, and not getting to do Boy Scouts with my best friend were also downers as a kid.
On the other hand, there are and were a lot of positives about growing up a Witness too. I won't go into them here so as not to draw the ire of the board.
Anyways my experience being a born-in I would rate as better than the average Witness and I am grateful to my parents for allowing me to make many of my own choices in life. (You may know that when the time came for it, my parents were uninvolved and didn't pressure me in any direction to attend or not to attend college and I applied and enrolled back in 1989 a few years before the softened stance towards higher education was implemented.)
As for the second question, I always had concerns and doubts about the Truth and the Organization growing up, so it wasn't a big surprise to finally conclude the fundamental fact of it all not being "The Truth." But it was surprising and interesting at the same time to learn all the little things and this continues to this day, each time something new is learned or something new develops in the Org.
-Eduardo