This will likely change through your real estate journey, but I always recommend starting with something in mind.

Quote from @Kody Smith: without getting too deep into my finances, what my strategy is...1. take loans to buy properties (leverage)2. fix/flip for day to day cash flow income3. use some of the fix/flip income to buy consistent cash flow through:- business acquisition, - commercial properties (MF and store fronts),I have no intention of doing ALL of the management myself, I will hire management as needed (medium term goal)my expected core role is money provider, evaluating the numbers, making decisions, and connecting with investors, wholesalers, lenders, contractors, and property owners.while I am just on step 2 of the journey, I am looking toward step 3 to stabilize, and not worry about if house prices drop mid project or not (or not worry as much) So to be fair this is more about obtaining and growing a real estate business not simply buying rentals for cashflow.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

@Toby Khan I’m not positive honestly, best bet would be to reach out to them.

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.  

My wife and I are starting our journey with our first STR and I wanted to ask: Should we use an LLC for our Airbnb, or would an umbrella policy on top of our current insurance policy suffice?

The distance and detachment is too much to make it worth it at this point in your journey, not knowing much about what you want to do.

Good luck on your journey and I hope you provide the financial security you hope for to your daughters. 

Your best bet since your working on your capital are going to be to use low money down hard-money lender.

My name is Christian and I'm excited to be here as I start on my journey into real estate wholesaling, specifically in the Pittsburgh, PA area.