Congrats - at the end of the day, learning all those lessons really require jumping in and "doing" and making the actual mistakes - no shortcuts and way to "learn" these by studying endlessly without making the leap

For SD IRAs custodians are required.  

When the property is refinanced a year later, after it has been owner occupied for the required amount of time, will the rate then increase to that of an investment property?

All of these things would require you to see all of his financials on the property and then be able to calculate it all out.  

Is it still legal to wholesale properties in Ohio or have the laws changed requiring a real estate license in all transactions such as in the state of Illinois?

Out of state is a crap shoot—you are putting a lot/all of the execution out of your hand so it’s dependent on you being able to identify good operators (which requires experience).

He has a landlord reference of five years.My policy is to require three months of rent in advance, which is plenty of time for him to find employment or prove his ability to pay rent on time.

They both require the same investment, $10k.Conservatively, you anticipate in 10 years that the property will not receive ANY appreciation.

Most tenants are happy to pay it because they understand a broken contract comes with penalties.My agreement requires them to participate in showings to potential renters during their final 30 days.

You need a set of specifications and a scope of work so that the work performed can be compared to the work required by your agreement.