Safe or Sorry: this is my Question

What is the difference between parasailing and paragliding?  In the first, semi-adventurous tourists put on a parachute and are towed behind a speed boat; while paragliding requires a level of moxie that few people have. Enthusiasts hike to the top of cliffs and throw themselves off, depending on a flimsy nylon parachute to slow their accelerated rate of descent. What kind of fool would choose this for recreation? Me, I hope—if I had known then what I live now.

If at, say, 25, I followed Alice down the rabbit hole and was given a glimpse of my life at 45 would I have suddenly gained the internal fortitude to do all types of seemingly crazy things. It is one of those 'road less traveled,' right turn/left turn questions that philosophers have chewed over for ever. I am more interested in imaging the kinds of things that I passed over-thinking I could always get to it later.
These thoughts were triggered by a video I saw of a couple hiking through a South American jungle with the sole purpose to jump off a cliff. The wife is having so much fun, she does a back flip off the edge. The husband gets caught in a wind current and slams into a tree. Even after a severely broken leg from this accident, a year later he is eagerly planning his next jump. Crazy? Absolutely, but, at the same time, so darned alive. If I had my health back I think I would start with bungee jumping, move to paragliding, and 'take the leap' to base jumping (same jump, no chute). Not because I had my full functioning body back, but because being safe and sensible doesn't guarantee that you will be safe or that life will be sensible.
Would I rather: be a quad from hitting my head on the ocean floor or sit safely in the boat; eat the volcanic Thai food or stick with the one star; take the payment optional roving reporter job or settle in to editors desk. I often say that except for MS, John and I would be backpacking now. In reality, we had plenty of health years where we were too busy, too parents, too career to take a weekend day-hike trip, let alone a summer to reclaim the Pacific Crest Trail.
This isn't about regret—rather a touchstone to return to the next time I make a seemingly small choice or awesomely large decision. My paragliding, hiking, and volcanic food (and roller derby-too bad) days are behind me, but who knows what is ahead. Maybe the next time I find myself in an island locale, I will sign up for the parasailing.