Now as I approach 40 I see clearly that had I started right away I'd probably be living on an island now.  

The properties I am bidding on are generally 80+ years old so it's mostly to protect me from fire damage and foundation issues, but I can see the merit in your approach. 

Hello BP:I’ve been approached by a professional who would like to lease one of my apartments and utilize it for AirBnB.

Doesn't seem like there is much interest from agents or property managers to get on board with another client, am I taking the wrong approach to this? 

There were several problems with this approach.

It was a  smaller house(2 bed 1 bath) only got rented for $525, its currently rented at 550(same tenant for 4 years). 2014 Rental #3 - Neighbor of rental number one approached me, they were looking to down size into a trailer for some reason. 3 bedroom 1.5 bath and 2 car garage for 27,500.

Especially now that you're approaching the one year mark, you should be able to do a cash out refi at 80% of appraised value. 

We found we were able to roll over the funds brought from a previous employer. 

I realize this is a lawyer question, but wondering how others have approached this situation. 

I like that approach!