It ended up being one of the scariest experiences of her life and was literally chased by not one but two different groups of what she described as gang members. 

My busy life has caused me to become complacent in my RE endeavors but no excuses!

I'm 30nyears old and just now restarting my life. my passion for real estate is what has led me to this forum.

I want to run this for 8 years or so, not life time and use this as sort of insurance income if and when things get rough.

Of course they have to be sure that you ASSUME THAT MOST PEOPLE MAKE NOTHING with their programs before you hand them your life savings.

What are the general thoughts in owning a single family or even small multi family and generating income thru VRBO/Airbnb?

Life is too short.

Now I know that should be a deal breaker but they were very upfront and from the looks of it they let someone in there life that scammed them badly.

Obviously, as your progress through life, you need to increase your reserve to match additional living expenses. 

Even when buying multiple properties from the same seller at the same time, pretty much everything now is one to one - meaning one parcel, one contract.I've bought and sold a decent amount of properties, many purchases were directly from financial institutions, however there is only 1 occurrence in my life (7 years ago) that I purchased a bundle of assets on the same contract - and half of those assets were total garbage and the deal was a disaster.