However, what if you prefer simplicity, limited risk, and are living off of the income? 

Consider offering equity partnerships, debt financing with profit sharing, or preferred equity, where investors get a fixed return before you share profits.

How do 5-7 people share food space, kitchenware, cooking time, etc?

I have some clients who prefer to have a PM for maintenance/contact/rent collection/general management and will place tenants and write leases for themselves in exchange for a reduced rate.  

Sounds like you've found a reliable resource for SBLOC, but what you are describing almost sounds like preferred equity as well. 

Normally, my preference would be a Duplex for ease of learning, but after looking at the price point in a place like Cleveland, I theoretically could purchase two Single Family's there.

We recently signed up with Steadily, which is the preferred insurance partner of FurnishedFinder.

Yes, as I'm doing more research, I'm finding that I would prefer to invest in markets that I know personally, so as not to rely on external variables completely.

We would have preferred to work with them within reason to make it a quicker and easier process.

I prefer to stay further from the coast and hopefully further from major storm/flooding events (potentially lower insurance costs).