I want to know specifically any insight anyone might have that would give me some clarity of perspective on what I can do to start acquiring property and becoming better at deal evaluating

Looking at:Estimate Rent/ incomeMortgage, tax, insuranceVacancy (10%)Maintenance (5%)Cap X (5%)Property management (10%)Evaluating by rent to value % , cash on cash %, ROIAm I missing or overlooking anything?

I’d contact a drainage contractor for an evaluation of what is causing the crawl space water problem and an insulation contractor for the vapor barrier plus replacement of any inevitable insulation collapse from crawlspace water.

I don't agree that having experience self-managing necessarily gives you all that much insight into evaluating a property manager, because a property manager isn't JUST managing your property or properties... they are managing many (often hundreds) more for many other clients, and they are running a business. 

and list all your numbers for more experienced people to evaluate here on BP. 

When evaluating passive deals I look at sponsor first, deal second.

Evaluate each bid and select the sub that you feel is the best fit for you and the job you are asking them to do.

I am here to evaluate potential neighborhoods for a rental investment.

As @Taylor L. stated, the sponsor's track record is the first step to evaluate.

My personal preference having thoroughly looked and evaluated houses in both markets, is Arrowhead.