Good post, UCGal. You’re right, it really does depend on one’s stage in life, familial obligations, future employment/income prospects, etc.
What ER said is true about the yo-yo types who make incredible amounts of money on a lucky streak, but then double down and lose everything (and then some). Sometimes, they actually manage to come back again, but they usually crash again, too. Some might view this is “successful” because when these people are at the top, they can really fly high, but they can crash just as dramatically; and seeing this — more often than not — is what makes me want to do the exact opposite of what these people do, and what they invariably do is use leverage…lots of it (and get into really convoluted deals that don’t make any sense).
