I'm not a fan of wasting time, so to stop myself before I get in way over my head I want advice to either validate or constructively criticize where my head is at.How would someone who has been success in this field navigate their learning path?

Checkbook control was critical to me.

You should discuss this with your CPA to see how it would affect your parents and you and your brother before you proceed (critical). 

Of critical importance is your Reserve Funding Plan...be sure you have a complete understanding of what the numbers truly mean and how those numbers are arrived at, and if they are currently reasonable numbers.Check for a local chapter of the Community Association Institute and join up!

Therefore, we need to regulate and tax carrots.I swear, critical thinking is a lost skill.  

So, my cash flow has doubled on the way to tripling, along with that forced appreciation.I critically look at my deals, with a shark tank scrutiny to bring myself, wife, mom, dad, and my investors a financially free future.  

I think a critical part of your due diligence has to be determining what the chances are of it becoming occupied again. 

Taking action is critical.  

For me, a delta of ~one month is not critical.

Please don't take this as criticism ... just advice coming from a place of helpfulness:1.