Interesting question this and something I've pondered for a good while now.
I'd have to say yes I'd do it all over again subject to the provisos that I retained everything I've learnt over the years and had the free will to make different choices in certain instances.
The conundrum: if this was possible would you end up being the same person? In my case I have come to accept the mistakes I've made (and it's taken a while for me to understand and accept that such mistakes made were actually justified in some instances and in other instances even fun). And I have actually come to like who I am (although I know quite a few people who would disagree with my notion but I've also finally come to the realization that those people can go and get fucked). I just don't like where I've ended up in life (and this mainly due to certain circumstances or events within the last two or so years that really were beyond my control nor was I the cause of such).
If you're talking about a TOTAL reset i.e. start from the beginning, knowing nothing, and taking a gamble on how your life MAY turn out: well then I'd have to say no thanks.
Of course and if you're that way inclined and bring theism into this: well then that changes the picture somewhat. Many believe that all of this is just a "test" and that we "chose" our path before we even arrived here. I've spent the better part of a year trying to make some sense of the theist vs. atheist points of view on this (where we come from, why we're here, and where we're going after death). Sadly: the atheist points of view are winning the battle at the moment. With all the stories and posts I've read of people who have had the most horrendous of childhoods and torrid lives: if it were true that this was all a "test" and that we "chose" our path well then those people are either far braver that I, more stupid and illogical than I'll ever be, or masochists (or, at the very outset, their "reward" at the end will be greater than mine).
There's also the reincarnation argument though which I find interesting (although my personal "jury" is still in deliberations on this issue so I cannot contribute much more on this).
Anyway. If anything I've posted above resonates with you or you could be bothered to be looking for possible answers (but with the warning that it may confuse matters even more and detract from the topic at hand) then take a look, on YouTube, at some of the lectures and presentations by Christopher Hitchens or debates between Christopher Hitchens and [insert name of theist here]. Richard Dawkins being notable as well.