We've been bankrupt on, burned, etc and even ones that do a good job for one or two, eventually drop the ball and are fired.

I moved to Cleveland in the early 80s and the city went bankrupt.

I have long said that if I had a financial calamity (jobless, bankrupt, etc.)

I heard another investor joke once that if you purchase too many "great deals" that have negative cash flows you'll make yourself bankrupt. 

So yes, they got the property but it was half finished or completely gutted, they couldn't find anyone to work on it, and much of what had been done hadn't been permitted so they found the properties that they received as security pretty much useless or requiring so much money to finish that it caused them to go bankrupt.   

Investing is not a smooth road and when the bumps hit the last thing you want is bad debt hanging over your head that can, and often will, bankrupt investors.

The trade off for that is twofold; a static interest rate for the next thirty years, vs a slightly lower, but variable interest rate on a HELOC that could be 15% in five years, which would likely bankrupt most investors. 

That's how I'm approaching this challenge, prepare as you mentioned by learning from others but then taking the leap and inevitably making a few mistakes of my own.Admirable and manly as this list of professional achievements is, there's nothing here about overcoming serious mistakes, about being laughed at, ridiculed, successfully taken advantage of, bankrupted, stripped of your illusions, broken on the wheel of life, and still finding a way to come back from shame and personal failure.You're going to need some of that, Gregory.

A long-time resident at where I'm now living told me when a previous owner (that went bankrupt) started accepting HUD tenants, "that's when the drugs came in" (I wasn't living here then to be able to confirm this assertion, but I have no reason to doubt it).The same reaction happens in business ("street fighting" and "lifeboat ethics").

I've done 4 startups and that was totally fun - two went public, one went bankrupt, one got acquired.