@Jerell Edmonds is right that many of us, including myself, waited because of fear and feelings. 

Is it fear of losing money?

As soon as you act decisively, demonstrate no fear, do not coward to his threats, and make it clear that you are managing to the lease without concession, he will stop thumbing his chest and making crazy demands.  

Fear of the unknown. 

@Benjamin YingNo one thing or person can give you confidence to overcome the fears of buying an investment.

What I fear about that set is what happens when Josh wants to get a new job? 

While I don't have ideas on compelling Airbnb to do the right thing (unless you have national news reporter friends), what you've reported is one of my fears and you've had a great and successful history of bookings so far.

I needed to prove to myself that it’s possible to go after the larger deals without holding back due to fear or lack of confidence.

Then some people are frozen with fear of regulation and who don't do any deals or stick to investor loans.It's not actually difficult or scary to get it right.

BiggerPockets is a fantastic resource.What's your biggest question or fear as you start your REI journey?