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

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.

Honestly, I still feel broke, My previous job 4-5 years back was 200kplus/yr (Subsea Engineer Offshore).

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.

I have already ran all utilities from my original rehab budget but need about 30k more to finish.Now im 22 and really took the gamble putting most of my money into the original deal so savings isn't really an option.

Common illegal activities are involvement in drugs, subleasing the property without prior approval, illegal gaming or gambling, cockfights.Holding overA holdover tenant is someone who continues to stay in the rented property without the consent of the landlord even if the lease has already expired or has been terminated.

Even if you're aiming for appreciation and want to hold more than five years, you'll still be gambling a little bit basing your purchase on Micron.