I would prefer not to have to commit to an agent at this time, so an individual who has great real estate experience but is not a realtor is preferred.

If you find one who has rental properties and has first hand experience that can be VERY helpful.The conflict of interest is a common question, but really a non-issue if you consider the size of the market and how many properties an agent can buy.My team and I work with a lot of investors and yes I personally buy a handful of properties every year, but there are about 30,000 transactions every year in Milwaukee.

I am using my own money, sitting in my checking account, and loaning it privately to individuals who I deem qualified to borrow it.  

I've enjoyed his content and practical advice - can anyone share their experience with his course? 

In my opinion, I would not take the advice you received regarding using OPM is you have no experience in investing in real estate.I would also not look to be a private lender for several reasons1) You are better off putting your money with a corporate bond / CD and get 5-6% with little risk compared to 10% to 12% with much more risk given today's market conditions2) You won't be able to retire getting interest income, which you said is your goal.

You did not underwrite this on any of your offerings though, so you're speaking from direct experience not by observation. 

Does anyone have any experience / can advise on the process in each of these counties?

This is completely up to you, If an individual came around with perfect credit and met your other income requirements I assume you would rent to that person.

I have some single family rentals north of you in Delray, happy to share my experiences if you want! 

That individual now wants out of the year long lease.