It's a different animal all together to try and manage an out of state investment property. 

You have used home equity lines of credit to purchase investment rentals and want to know the best way to pay down the HELOCs.Between the two properties you bought, after expenses, you have $250 a month positive cashflow to use.What I like to do is pay down some principal every month with my positive cashflow.I use my extra active income from real estate commissions helping other investors to pay down the principal even more which just frees up that credit for me to use again.I know I can refinance the HELOC debt before it changes to principal and interest as it is just interest only payments as yours are.One difference is the cashflow, I have greater positive cashflow and could make the principal and interest payment in the future with the extra cashflow I already enjoy.I always get HELOCs on my income properties as well after purchasing them to pull out as much of my downpayment as possible.

My main goal is it be able to retire at age 40 from my main job and work entirely on my real estate portfolio.

I have my own thoughts on what the differences are, but I am biased so I'm curious -- as a listener to both shows what do you think differentiates the two (or should differentiate the two?).

I try to evaluate a unique property 2-3 different ways, then make a highly educated guess based on my knowledge of the market.

I'm excited about your presence.. are you open to different property types if the math works out?

How would the situation differ with a home that’s never been a STR but would become one, or a home that’s for sale now that is a current STR.

Change your story each month as different stories will resonate with different people AND use each story to emphasize one of your “who do you know…” questions.

I've looked at shared rooms for months in different Canadian cities noting price movement. 

I'm fine with doing some minor fixes and improvements to a property: Adding overhead lighting/fans, better flooring, maybe redoing a main bathroom.