Meanwhile I'm getting the education required to be an agent and will evaluate after completing the education on whether or not I want to move forward with 'taking the test.'

Just rent evaluate the market and then decide.

My strategy is to buy and hold multi-family properties and I am still currently evaluating different areas. 

Reaching out to the City to see the number of new construction permits, evaluating the area infrastructure, state of the market economy, determining whether the major industries players (aka employers) will remain intact due to Amazon effect, etc.My best!

@Duke Giordano a great first step to educating yourself (mission critical if you go this route) is to learn by evaluating deals.

How should I go about evaluating our 10 properties, and determine which I should hold on to and which I can sell for the cash I need.Should I sale multiple lower valued properties to get the cash I need, or one of the higher valued properties.

I would suggest utilizing one of the calculators on this site as they can be really useful in making sure you include all of the additional costs that come with being a landlord that way you can actually make sure the property will cashflow (if that is your goal) and it'll help you evaluate the deal overall.

Recommend further evaluation by a qualified roofing contractor.

If so, you should evaluate if the contents coverage is too high (may be an included amount so there may not be any option to lower it)

I'm currently evaluating a deal for a mid-size multifamily in between Allen Hills and Rockwell Park, and considering I've never even been to North Carolina (out of state investor), I wanted to get your opinions before I go deeper into it.How is this area?