Trying to overly simplify a complicated subject even further, could I safely say that not having enough reserves, because of a lack of planning for the worst and just assuming something will cover you later, will always burn you in the end (barring you just plain get lucky)?

Do you buy insurance on your house in case it burns down? 

Im 26 years old, I live in Denver and I’m a bit burned out in my current career path.

An ugly deal is something you lose more than money, you lose your will to keep going; maybe you get sued, maybe you buy a house at an auction with a mortgage on it, maybe you skip getting insurance to save money and the place burns down, etc. 

If you've been burned by the market, what happened?

Allowing tenants the flexibility to pay when they so choose inevitably leads to burned out owners. 

It burned down, so maybe that made it cheaper 😀.  

Would love any guidance on buying out of state -- from best markets to consider, to techniques for research, how not to get burned, is it OK to purchase sight unseen or would you always recommend viewing in person, etc.

Now it's all SPI owned land- private timber company that runs a vertical operation where they own the land, the mills, and operate the trucks- and the only Forest Service land that is logged is the burn areas after the forest fires come through... that maybe could have been prevented or better contained if the forests were managed... but that's a whole can of worms to open.

All I have to show for that investment is occasional emails in Japanese from a Tokyo bankrupcty court.I'd also like to warn anyone running around with money burning holes in their pocket to be very skeptical of "initial coin offerings"..