Sure, why not? I know I could end up living a really shitty life, but I'd be willing to take that risk. 

Nope. I play the best I can with the cards i've been dealt with.

Lets put it this way, if I got to keep my memories but had to do it before I turn 60 then I would definitely do it without thinking twice. If i didnt get to keep my memories then I dont see the point since it is the same as me just dying. If i got to keep my memories but had to do it right now, I wouldnt because right now I have yet to even lived this life why would I reset for a small chance at a better life and a much higher chance at a worse one.

Where do you think you'll end up, do you think you'll end up somewhere nice?

There's a possibility. The world's a shitty place, so probably not. 

I wouldn't because the only dice we can cast are the ones we cast after being born. In the beginning, we're being rolled for.

"The only thing that stays consistent for sure, is that you are human."
Hmm, so that mean.
Yeah!

There's a chance that you could reincarnate on another planet.
I mean, the rules don't have anything against that.
A life on a planet far away doesn't sound too bad.

Only way I would reroll would be if I got to start in the same year but had all my current knowledge as well. I have been far too lucky with my current life to gamble it away into something less fortunate.

I've no doubt there's complex life on other planets, but humans specifically? Even if there's intelligent life I'd think they'd be a completely different species. Basically I think Earth is the only place you'll find humans.

good luck wih that. There is no planet known so far better suited for humans than Earth.