I would probably re-roll the minute I am about to die. So maybe when I am 85 or so.

Well, if it's a no, then I definitely don't want to. I don't think the memories I have are something I'd contemplate putting a value on, or would be ready to exchange for anything, even if I get a good roll...

On the other hand... If I do have the memories, there's so much I'd be missing, from my old life, that could be depressing...

I'd say yes if I keep my memories and can go back at any time, would be awesome as something to try out XD

Purely on the quality of the roll, I think I've gotten pretty lucky... So, no, not something I'd want to do, regardless :p

I usually need 15+ re-rolls in Diablo III to get the stat I want on my items so I wouldn't risk it on something as important as my whole life.

It doesn't change my answer.
There's just so much that could go wrong.
No assurance that it'll all work out.

Though everything being said, I'd be tempted to take the jump.
So, how does one roll the dice?
What kind of process do I have to go through to do this.
That may affect my answer.

Oh, and does my body stay here, maybe I'm could meet myself?
Like, would there be two of me?
Would I have never existed, and would I be born at the same time as I was normally, or am I going to have to be born into the world as it is now?
Being born right now, doesn't seem too appealing to me.
At least I was born at a time where I could develop a sense of privacy, and, well awearness of just how messed up the future will be.
I don't think I could perceive the world and future as it is to me currently, if I was born right now.

Bro that's cheating xD that's just reincarnation 

Nah.
Obviously, my initial roll could have been much better, but I climbed to a position I am happy with and re-rolling is a risk I'd be unwilling to take.

Plus, I suck a rolling dice anyway.

In a heartbeat, i'd rather take the chance on a worse life than living with the kind of social-anxiety that keeps ruining my life

But what if you turned into a girl and wanted to be a boy :thinking: 

Score! As I say, as often as possible: "Beats squatting in the dirt waiting to die of thirst."

I quoted myself there. Just to be clear. It's a tough world.

I'm a Canadian with a wife, good job, and expecting twins before the end of the year.

I ain't rolling.