In a high demand low housing inventory environment like Oahu rents could have the potential to increase faster than less populated areas. 

I am not sure at what level it changed, but he was certain I could sell now if I wanted.  

@Charlie FitzgeraldPaying a lender off in full once you decide you no longer want to do what you said you would do is what you are supposed to do.Incidentally my first nomadic owner occupant flip, I tried to call it an investment property because that seemed like the box it intuitively best fit into (I still feel that this makes the most sense at a 'common sense' level).

Annette in my opinion it boils down to security and risk and your comfort level in those two areas. 

It would look similar to the house below, but on grade level.

You can do this by interviewing them to determine their track record and level of expertise.

What I am considering to help that go faster is renting out rooms in my primary residence (SFR).

Too many investors chasing too few properties and bidding up prices to levels where there's no money to be made.

And 36 Other Key Financial Measures" - the faster you can get to making data-driven decisions for everything, the better.Good luck on whatever path you take!

It was listed as an online auction with a low starting price.  1,320 sqft split level (4 levels).  4 bedrooms, 3 baths, formal living room, family room, unfinished basement, 2 car garage, and a fireplace.