That depends on you and your risk level really.

Just depends on your time and comfort level.

I'll take the faster approach from now on. 

100 year old low-mid income rental is not really expected to have perfectly level floors.. haha Sad, but true..

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.