There's no right answer.
By that, I mean everyone dies with regrets: regrets about living too wildly, regrets about living too conservatively, having kids, not having kids, missing out on an opportunity, or risking too much.
You're going to reach the end of your life and believe it's unfinished, it seems.
I have no advice. Make the best choice at the moment, with all you know at the time, and then forgive yourself for it, I guess.
It's hard to read this without hearing a "I got mine, so f everyone after me" in it. When you talk about this with your friends, maybe consider rephrasing it?