That whole topic always rubs me the wrong way. Taking risks could mean catching aids and dying, falling off the cliff, getting in racing accident, going bankrupt, etc... Except we don't hear the stories of those who risked and died or failed, only those who risked and succeeded.
I'm not saying you shouldn't take risks. I just have no idea how you can come up with rule or guideline that has any basis in reality. There are tons of people who took some risk and are living with the negative repercussions but we rarely like hearing about them.
You're thinking too hard about it. It's just like how guns don't come with a label that says, "Don't shoot yourself."
If you struggle with how to use regret minimization I'd say just see the rule above it: "Stop doing stupid shit." Your examples of "catching aids and dying, falling off the cliff, getting in racing accident, going bankrupt" mostly fall under doing stupid shit with the possible exception of going bankrupt, which could be due to bad luck (but is most often a result of doing stupid shit.)
People get in over their heads because they risk more than they're willing to lose and fail to think long-term, which is stupid shit. And often it's not just one bad decision, but a series of bad decisions that lead to catastrophic outcomes. I became a millionaire in my 20's by taking risks, but I never risked more than I was willing to lose--financially or in my marriage.
There's not a rule or decision framework for everything, at some point it comes down to common sense and judgement(which can be improved through learning). And even with our best efforts we'll make mistakes, which is expected. But it's ok to make a thousand small mistakes, you just have to avoid the big ones...like catching aids and dying, falling off the cliff, getting in racing accident...
It's not a recipe, it's a rough trajectory: some assembly (thought) required.
I'm not saying you shouldn't take risks. I just have no idea how you can come up with rule or guideline that has any basis in reality. There are tons of people who took some risk and are living with the negative repercussions but we rarely like hearing about them.