I understand I can increase liability in each individual landlord policy, but one single umbrella policy is much more cost effective when I have multiple properties.

You really want someone that invests in their market themselves and understands the numbers.

@James Wise I began investing in Cleveland (from NY) this year, and I was following this grading guide for a while!

It helped me to do more research and better understand that I’d like to buy property elsewhere and rent that out, rather than renting my current property.

Instead I want to take advantage of the opportunity I have of living rent free to invest my time and money in STR's to hopefully build that portfolio up and eventually make that my main source of income (I understand that will take time).

This will help you understand your options and decide if it's the right time to hire a pro. 

Quote from @Matthew Paul: I understand how businesses work.

I know that I will need a good realtor on my team that understands not just the market but the real estate investment industry itself.

If you are going to sell then you must understand the tax implications. 

Being a part of the local REIAs in both towns can help you understand more of what is going on.