It's essential to clearly define your goals.

2) Please define "above market upside in year two and beyond" as not understanding... 

Your goals will define the route you take on this but building a list for buyers/investors is a time-intensive activity and the list is a living and breathing document.

This will provide you two benefits:1) Help you better define the position, so you can hire a better matched person2) Make training the next person easier

Obviously this person would naturally have more %Regardless of what structure you guys decide on make sure it is clearly defined!

The participation must be regular, continuous, and substantial as defined by the IRS.

Under Declarant Control, which is defined in the CC&R's, the developer is the HOA Board. 

Simplify the structure as much as possible, have clear roles and responsibilities that are not overlapping (meaning only one person is allowed to make certain decisions) and a clearly defined exit plan.

This is defined as 30 days or more, and you will easily find nurses, professors, students, and more than need a 1-3 month airbnb.Speaking of, you could rent the whole space mid-term - and I suggest through airbnb or VRBO but you don't have to use those.

Regarding #2, do you have an example of what is defined as the "property code"?