Depending on the zip code I was wondering could I gamble with them on a fix and flip or brrr.

I'm ok with gambling on it.

A gamble on gambles of volatility moving certain ways in certain time windows..... 

At that point things are more of a gamble. 

REI - It's an exciting adventure filled with opportunities to learn and grow.

They cannot arbitrarily make wild gambles because they feel like it - they have to operate within established risk parameters that are approved by several regulatory bodies and internal controls.

My goal is to create generational wealth for my family and to eventually have the financial freedom to say "yes" to travel adventures as a family.

That's a gamble.

The client was willing to gamble on furnishing for STR over LTR route and we were good for 3.5 years, then one day the man came and shut it down. 

After 45 years investing across many asset classes, many investment types, and everything from lowest risk to outright gambles, I think I finally know the answer.The biggest divide is between investments in which operational control over that investment is with the investor, and investments in which control rests with another party.