The longer you hold onto it, the more your costs add up, the more costs you have to recover, and the fewer funds you have available to use to recover them with.Think of it like playing Poker (not because it's gambling...REI shouldn't be gambling). 

But yes, sadly most retail investors don't know what they're doing and end up gambling.4.

Right now my focus is simply to learn all I can and connect with people who are immersed in this world.

Be it stocks or real estate.If I want to gamble, I'll go to Vegas and loose quickly on the slots so I can have a cigar and enjoy a cocktail.Much success

Not, hey lets gamble since I love risk with 100k or more, and lets put my personal house, and car etc on line.

Over the last decade, that gamble paid off and significantly helped grow my net worth and investable cash.  

That's gambling people. 

My gamble is, about the time I get this cabin designed and built, the Airbnb market is back on the upswing.

This is where expert due diligence comes in, so as to avoid gambling away your business.Expert due diligence is crucial when it comes to business transactions.

That question will require an essay to answer every part of your question :) With stocks, you mostly gamble on appreciation.