I'm 44 years old (male) and like a lot of people my age, YA didn't really exist as a category when I was a teenager. You read children's books, then around 13 or so you started reading adult books. The last book I took out of the junior library was Alan Garner's The Owl Service as I'd read Red Shift (out of the adult library) and particularly wanted to read it. That was prompted by the entry on Garner in the Peter Nicholls/John Clute SF Encyclopedia which I bought in early 1980, so I was fifteen. (I'd previously read Garner's Elidor when I was ten.) Other notable books from then included Judith Guest's Ordinary People - not strictly speaking a YA, but now taught in schools I believe - after seeing the film version in 1981. Another one was Ursula Le Guin's Earthsea Trilogy, which was repackaged in one volume for adult readers around the same time.
Since then, I've read YAs on and off, usually the ones that crossed over to adults - Harry Potter, His Dark Materials, The Strange Case of the Dog in the Night-Time. In the last two or three years I've been making a point to read a lot more YA if I'm going to be writing it - and I've read some terrific novels as a result. I find the best YAs very engaging and far less padded than many adult novels.
I think that YA is increasingly given a lot of respect - a watershed in the UK would be the major literary prizes that The Amber Spyglass and The Strange Case... won, against adult competition. Writers like David Almond (who may count as MG rather than YA) have rock-solid critical reputations. But the best children's and YA writers have always had adult readerships - certainly true of Garner and Le Guin and others. I don't think YA has a reputation for being "girly fodder" - not that there's anything wrong with books aimed squarely at teenage girls. Writers like Jacqueline Wilson and Louise Rennison sell by the truckload to them - and possibly cross over less than other types of YA do to adults. The more common impression I find with people unfamiliar with YA fiction is that they think it's sanitised and overtly moralistic in a very simplistic way - not true at all, as we all know. (How many times has this forum had threads asking if you can have sex and/or swear in a YA novel?)
As for me, I first wrote a YA novel by accident. I wrote a novel with two seventeen-year-old girl protagonists when I was myself seventeen. I revised it seven years later and sent it out, thinking it was just a general contemporary novel. An agent picked it up and submitted it as a teenage novel. I was very surprised by that, thinking - very naively - that it couldn't be teenage because it had sex and swearing in it. (I only had that agent for ten months - the novel got rejected, she left the company and no-one else wanted to take me on, so I lost representation.)
I do write adult fiction - my publications so far are all short fiction, with a now out-of-print collection appearing six years ago. However, I do find that I'm often writing about characters in sixth form or university (equivalent to US high school junior/senior or college) or at most early twenties - I clearly have unfinished business around those ages. Are these characters like myself? Only in the sense that every character is like some part of yourself. I may be male, but my male characters are no closer to me than my female ones are. But then in real life I have women friends I have more in common with than some men I know.
To answer your question, my late teenage years were pretty horrible actually and my self-esteem was non-existent.
The gender question I've answered at greater length in the "Writing from the Opposite Gender" thread, so I won't repeat myself too much here. I've sold fiction written first-person-female to female editors, so I guess that I haven't got it too wrong. I went to a boy's school and don't have a sister - but on the other hand in University (doing an English degree) and at work I've consistently been in an environment where there are more women than men. At present I'm one of two men in an office of fifteen people, with a female manager - so I guess a lot comes in by observation and a kind of osmosis. (I'd be a lot more wary about writing from the point of view of someone of a different race, for example.) It's an advantage here to belong to a writers' group which has always been around 50/50 female to male, so if I do get something wrong someone will tell me! As for the teenage thing, when the YA novel in my sig is ready, I'd hope that some of the teenagers in this forum would do a beta swap with me, though this won't be until much later this year. (I've already beta-ed a novel by one teenage writer here, earlier this year.)