I don't mind gambling a small fee to each interesting property to discover whether or not there is a problem, but to stumble into a million dollar liability will end me.

It also comes down to goals if you in Seattle and do a Heloc or refi just know your doing it for appreciation (which I call gambling) but others will call investing.

Dimon, et al. feel that it is their right to gamble totally unregulated while still being backed by the tax payer if their bets fail? 

Hi Nate,I think you have chosen a good place to start your investing.  

That's not a gamble I would be willing to take.

You are right this one kind of is a gamble but what can I do now, other than change the decisions that I make in the future.

When you lose your link I guess you simply sit in the dark in your closet and pray to your chosen deity that a miracle will soon happen.Seriously sounds like a major advancement, like the car industry, where no one can repair their own home and repairs will be extremely expensive.

That is called gambling.

If I could start it all over again, I would have chosen to vacant the property before selling it. 1.

You have just chosen to interpret any advice you didn't care for as negative.