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.

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.

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

If you already come with the experience (i.e) r/e background experience, don't need one.

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

I think I'll just look at this as a learning experience for how I operate going forward and take my chances on having it appraised as is.

As a seasoned real estate agent with five years of experience under my belt, I've had the privilege of guiding numerous clients through their own investment journeys.

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

Guest experience is one of my favorite STR topics!

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