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.  

From what I've heard, local banks are sometimes more flexible than the big guys.A buddy of mine managed to snag a HELOC on his rental property, which isn't always straightforward, but it opened doors for him.

I think it’s more about being flexible with your numbers.

Your situation offers a lot of flexibility, which is a great position to be in.

If they have money and can compete on pricing, brokers will be the best bet.  

Hi Joe,I think going with a LOC is going to provide you with more flexibility than going through the process of obtaining financing for a purchase transaction.

Sometimes it’s about being a little flexible on location or property type.But enough about me: Where do you see your first property purchase happening, and what’s your biggest question right now about making that leap?

In a soft insurance market, coverage is usually broader, lower deductibles are more accessible, underwriting is usually more flexible, and premiums are generally aggressive / lower. 

The key will be to remain flexible, understand the local market dynamics, and position themselves to take advantage of the eventual boom when the project comes to life in 2025.

The current option that we are looking at is buy, live in 1-2 months of the year, convert to MTR or STR for the other months (especially since we are flexible on our end).