However, I do have a connection who can help manage your Citrus Spring property as well. 

Well done!

I would look into assets that are non-correlated to the stock market or real estate, as well as tax advantaged assets to help shelter your income. 

I also suggest you post your listing to "Short Term Rental Listing Advice" on Facebook and let them give you more feedback as well.  

So I said, "well, if that isn't the path, what is the better approach?"

Those couple hours of research will save you hundreds of hours of time down the line, so it's well worth the effort.

To add value to the property, we undertook extensive renovations including the removal of over 40 yards of trash, installation of a new septic system and wall-hung boiler, and a new well pump.

We have our primary In a trust but thinking if it's a good idea to buy the rental in a trust as well.

Quote from @Trent Reeve: well, a company would have to 50 states and build in integration functionality for 50 different systems.

I know a few investors that do it here in Tempe, Mesa, and Glendale - not to mention you can do it in Phoenix as well.