I kinda feel like my rentals are doing pretty good, but am wondering about some kind of objective measurement that verifies or contradicts what I think. 

With some attachment to the home, its hard for me to be objective.

You should then have a really strong amount of cash flow to satisfy your main objective which is to pay down student loans.

Do you want to become a RE Investor, own a business, what are you passionate about - what would you do if money is no object? 

We'd prefer to grow our business in our current market, but clearly rent to ARV rates are out of balance when compared to our objectives.  

I believe I got sidetracked by various people throughout my education process and the flip started to become the "shiny object" that could easily derail me.

Even if you were able to find coverage in your current policy, the damage would need to be cause by a cover Peril, such as Fire, Falling object, etc.  

https://www.jcs.mil/Portals/36/Documents/Doctrine/pubs/jp5_0_20171606.pdfGoals (objectives) drive the plan.

I am still reading non RE related books (currently loving the Power of Focus and then onto How to Win Friends and Influence People), but I have felt a lot less distraction/shiny object syndrome, and am working through all my goals for 2020.I would love to hear other BP members thoughts or feedback on how they handle all of the content out there and what strategies you have found to help you stay focused and not be overwhelmed by all of the different opinions/ideas on REI.

I would buy it with home equity credit / loan and the payments will be higher than traditional lending, so not sure I could achieve the objective of covering costs.