Not sure whether you ultimately invested here and know nothing about Simm Capital but based on what you shared the first question you should be asking Simm Capital is where do the 10% dividends derive from?

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

My first move is a rental property, but BRRRR and Flips are the ultimate goal.Anyone have recommendations for contractors, boots, property managment companies, agents, insurance companies, or inspectors in Cleveland?

Ultimately, trust your instincts and choose a property manager who demonstrates professionalism, integrity, and a commitment to maximizing the value of your investment.

But ultimately, know this, no matter who you hire, you are the person who's ultimately responsible for your own signature.

They are ultimately the same thing but I know that many lenders require seasoning.   

Yes, buying is the ultimate end goal.

Ultimately, I'd be paying a down payment for a home, which then commits me to paying a mortgage when I could use that same money to buy another rental property that makes me a ton of cash. 

I ultimately settled on Columbus, OH as my target market and have been pretty happy with my decision.

This is when you hear stories about how individuals in their early to mid-20s ultimately give up because they're burnt out and have little results to show.