Here is a good video The Ohio Division of Real Estate made about wholesaling in Ohio https://www.com.ohio.gov/real/ I recommend you just get your real estate sales license.

I would highly recommend doing a renovation loan like the 203k or homestyle - you are able to leverage SO MUCH CASH for such a low down payment. 

Rhino is an insurance program, and I do not recommend them.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I’m curious if anyone would recommend to not post a listing at this time of the year, as it hurts the listing by sitting and you lose a lot of the “New Listing!”

- Any lessons learned or best practices you’d recommend for someone leaning toward this approach?

Personal recommendations don't always work.

I've seen the Speed Queen SF series recommended in a few places.

I would recommend keeping them, and gradually increasing rent on par with market increase + 1 to 2%.You could get a better qualified tenant, but they could be worse with money management, property respect, etc.