These people play by different rules,  don't think you'll be an exception, you won't.. you'll just learn why people like me are so salty! 

So its a long term play for us.

I’m considering two separate options for the rental, depending on cost/pay off:-Simply reconfigure the layout and make it more functional and appealing to renters.Or-Add square footage (possibly a bed/bath) and hopefully increase the value, functionality, and what it could bring in for rent.But seeing as how this is my first investment property my gut is telling me to play it a little more conservative and let these ideas simmer before pulling the trigger.

I spent a few years playing hockey near there.

The cashflow play on Oahu is extremely challenging.

I am using real estate for long term retirement play. 

Since the seller has likely already signed an exclusive representation deal with their agent, you either abide by their rules or don't play.  

As a multifamily investor, you absolutely do not need a license because it is a whole different playing field with commercial real estate.

The second is it actually incentivizes tenants to stay put because if they move, they will most likely be paying a larger premium.Definitely an appreciation play. 

We need to take the high-school attitudes out of play, and understand that every problem does have a solution, even if everyone is not happy.However, depending on the attitude of the complainer, I can get nasty too.