@Sean Dillon figure out how to buy a 2-4 unit with FHA loan.Then rent at least one of the units long-term for stable cashflow.Try STR in another unit as well as the other bedrooms in the unit you live in.You may even consider living in the basement, attic or worse unit in the building to rent everything else out and max cashflow. 

What are your thoughts on Cleveland as a place to begin investing and What areas would you recommend I begin looking at?

If you are looking for cash flow, I would look at a 4-plex.

To keep these approvals valid, developments should secure public investment to support housing affordability and ensure that at least 50% of the units are affordable.

I'm a 2x house hacker here in LA and an out of state investor.

If you are looking to purchase in an A or B neighborhood for under 300k in said city you are looking at either the 3 C's (Cleveland,Columbus,Cincinnati), Pittsburgh, or Detroit for starters.

3) What ROI are you looking for?

Now, are you planning to house-hack and live in one unit, or going full rental?

For a single property, a strong umbrella insurance policy may offer sufficient protection at a lower cost.

Quote from @Veronica Mitchell: Yes, I'm looking at 4 plex units renting the three and living in the other interested in the more up and coming areas.