Until we get some common sense into lawmakers where they begin to grasp the true impact their policies are having on the average worker, there will be no turning this around.

Then look up the following criteria:Unemployment ratesPopulation growthAge range population changes Median rent ratesVacancy ratesPercentage of job sectors (says be careful in areas that have one dominant sector +25% bc if that sector tanks it will most likely have a neg impact on rents)Top employers (same as above)The you take that data and observe the trend over the last 5 years to try and get a good grasp on how that area is trending.

Sounds like you have let the tenant know multiple times that they should contact the PM with issues and they aren't grasping the concept so unfortunately you need to train them. 

But that's my plan once financial freedom is within my grasp.

Call around until you find a lender who grasps fully what you are trying to do and offers a loan product that fits. 

I understood it enough to grasp the concept so that helps a lot.

I do not see anyone talk about Kelly Criterion on Biggerpockets, but it is really good to play around with building some simple models with it to grasp what growth rate you want coupled with the risk that you are comfortable with this. 

My other concern right now is getting a grasp on financial aspects of buying property.

Analysis of properties is still a new thing to me although the general concepts I feel I'm grasping quickly.

What @Ryland Taniguchi says is absolutely correct, although I would caution him in that a beginner to the real estate scene won't necessarily have an instant grasp of the jargon.