If the markets perform as predicted, the initial poor cash flow market will benefit from higher increasing rents and eventually have better cash flow than the market that had the initial better cash flow, but was expected to have less rent appreciation.In your local market it is easier to build and maintain your team, you have local first hand RE market knowledge, and you can more easily perform heroics if it is ever necessary.I recommend you take a second and third look at your local market. 

When evaluating a market, you should look for more than cash flow.

Looking for input on a couple of topics -Do we evaluate the deal as three individual duplexes or as a six unit property? 

I'm leaning toward hanging onto the property for the next five years and re-evaluate my position then.

My next step is to possible Air BnB proof it with certain locked cabinets and locked storage space that will allow me to easily prepare it for AirBnB on the weekends.

This is one of the old recommendations from senior military folks, buy everywhere you are stationed and then rent it when you move.So here is the real question, how would I evaluate/analyze my house for renting using one of the calculators? 

This vacation rental easily sleeps 8 people.

Even if you don't 'need' to leverage, each deal should be evaluated case by case.I will still utilize debt when cash doesn't help get a discount or help acquire a new property that doesn't check all the lending boxes.

When evaluating finishings or additions to a property you are looking to rent what are some ways you determine what is going to provide the best return and what is just going to eat into your investment?

From the phone discussion I think that the evaluation didn’t consider the additional ‘value’ to the structure.