Best of luck in your big decision and life transition! 

definitely will need to factor this into my decisions

The upside is that the seller gets a real written offer, and sometimes sellers can make surprising decisions based on real offers in their hands.

If I self manage(which was what I was planning) it could turn out a big headache) there are a lot of condos for sale which is a bit alarming as well.I would be self managing from California so that’s long distance management and may consist of many flights taking care of any necessities.Why can’t this be an easier decision lol good luck!

We advise clients to stay away from these zones on Oahu, or at least make sure they pencil as a long term rental before making any big decisions.

Build a relationship with one that you know you can trust to give you good estimates, and it will make decision making a lot easier.

Look at your investment decisions holistically. 

Keep in mind the decision making criteria is different for your primary residence versus an investment.

It feels like that the decision to add would be well worth the investment for monthly income but also my ability to sell later. 

Good luck however you are 100% incorrect,  You're opinion is just as valid as mine.