They mentioned how Dom helped them narrow down neighborhoods for a multi-family purchase and even flagged potential zoning issues before they made an offer.

The property has a massive 900+ sq ft attic with very tall ceilings that would make a perfect 3rd unit potentially grossing another $1000 per month. 

Basically, the further you get away from the city the more potential for cashflow, but you're also dealing with a different tenant base that may be tougher to manage.

Getting one property and cashflowing it will be a challenge. you can try seller financing but you are still going to be highly levered which just enhances the risk that you are taking on.The best way to grow is to focus on managing your rental, saving money through your W2 and crushing that - if you are a realtor you will make more crushing it as being a realtor than over leveraging real estate - then save for down payment and buy slowly. its not a rush.

Oftentimes my initial consultation call with a potential client runs 1 hr and that still doesn't give me enough time to cover everything about the STR market on O'ahu.  1.  

Seems like a low risk strategy for you to start taking action on your dreams, which is the crucial ingredient towards reaching FI. 

You can call it lazy, but perhaps also they don't have the resources to take on the potential number of small cases like this.

Can you articulate the risks you believe you will  protect against and more importantly how this Wyoming LLC will aid in your objective?  

Seasonal Slowdown (With a Twist)The holidays always lead to a slower rental market as potential tenants prioritize family, travel, and gift-giving over finding a new home.

You need to know how to manage risk.