And I'm concentrating on Lake County as I'm familiar with the area some and have ties to the Navy base which may provide a competitive edge.

If you don't own the house yet, you really need to pay the guy otherwise it's a waste of his time.Sometimes roofers and pools companies will give an estimate based on google maps. 

The issue I run into, based on what I can put down, is that I would most likely have to split the mortgage down the middle (I pay half/Tenant pays half) based on current rental rates and current mortgage rates (considering what I can put down).

@Jordan McDonald I'm based in Dallas Fort Worth.

I currently house hack with a SFH, but I'm researching ti decide what my next RE project should be based on my preference and market demands.

The coverage you need will vary based on the assets covered under the umbrella.

I would look into your local REI Facebook group and search for previous posts of people looking for property management companies.

I've been searching but could not find this exact question.

You looked at Zillow, which is notorious for being inaccurate, so if it is worth more and you are going based on that, who am I to disagree?

Zillow, apartments.com, outreach to local companies that common sense suggests would have project based 1-3 month employees.