In that case, you’d typically need to file a legal challenge, which could involve going to court and showing that the restriction is unnecessary or unreasonable.The best advice I can give would be to consult a real estate attorney to understand your specific situation and options.

My wife also made it clear that if we were going to expand beyond what we already own, she didn’t want to be involved in managing them.

Airbnb gives you the best bet at getting both. 

You can just answer it without the jazz, and I bet you know a few places right off top of head where people WANT to live, right. 

I know your involved at a high level with Board of Realtors and state regulators .. 

The single biggest issue in my way currently is obtaining enough cash, whether it be my own, or through partnerships or family/friend-based lending (which I am very hesitant about to begin with as this could potentially strain relationships unnecessarily when money is involved).

You bet it is lower risk than being on the equity side.

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

The quicker you can take action on the high dollar value decsions the quicker you will be able to grow.For sure take the time to setup the right foundation, but keeping it simple and easy when you are getting going is a safe bet!

My name is Nico Banuelos, and I've been actively involved in real estate since 2021.