@Ysabel Yow As someone who grew up poor and once lived in C/D housing, when I was younger I would wonder why landlords wouldn't offer better properties, I considered them Slumlords at the time not understanding how their business goals were prioritized.

Shemin immediately appeared in my mental, "I trust this person/organization" list. 

@Paul SandhuI've heard of that strategy but my husband is averse to it... he's risk averse to a lot of stuff but it balances my Ready, Fire, Aim mentality.

Someone else on here calls them "borderline mentally ill". 

Travel is a huge component as well, something I've prioritized.

I keep a lovely mental portfolio of missed opportunities that I have spotted and someone else has made money on. 

Knowing and acknowledging this mental barrier helped.  

Also, if you've already racked up 100 five-star reviews, your approach may be different than if you're just starting out where you may be prioritizing quantity of bookings over getting the highest rates (at least until you get more reviews). 

I can recognize in myself that their are some nerves and apprehension coming into play, and I guess I figure the best way to get over the mental/emotional hurdles is to educate and prepare.

I am not saying hand-outs or reverse discrimination, dependence causes mental and financial slavery.