You also need to get a grasp of the personality and culture of the HOA.

Honestly I’ve been wanting to avoid the voluntary servitude but maybe I should just grasp a different viewpoint until I dont have to anymore. 

I am educating myself on developing a scope of work and I know after a couple of deals I will start to grasp the numbers better.

I want to get a good grasp of where to start before considering something big. 

It seems to me that you have been living life like a high roller and you are at that point in your life where you need to just downgrade and live well within or below your means and get a grasp on your finances. 

. :)  I'm trying to get a better grasp of "best practices" for owning / managing rentals. :) Lease Terms: Long Term, One Year, Section 8, Six Months - does that mean "long term" for one year, and "Section 8" for six months, or does that mean, "Hey, as long as you pay on time, we're easy to get along with... two year lease, annual, Section 8, or short-term of six months... whatever you prefer, Mr/Mrs Tenant..." ? 

Yeah I'm working with an agent, but I'm pretty new to all of these concepts so I'm just trying to get a grasp of how to do this stuff on my own to get a general idea when I see something come up.  

Once you have a good grasp on that, you can assess the risk of a REIT or regional player.

But what I failed to grasp, and many others seem to miss too, is: Real estate, either passive or active, is only an investment if you work at it.  

@Joseph Crunkilton in my experience you just need to know your market very well to have a good grasp on the ARV for your potential BRRRR.