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.  

While I've made several investments independently, what sets SDIRA Wealth apart for me is their competitive pricing, focus on new construction, and access to markets with better performance compared to my local area in New York.

If you could furnish the rooms, I'd say that is best bet for cash flow.

Some of the best opportunities can be found in other regions, particularly in markets known for strong rental performance, stable property values, and tenant demand.

Start by leveraging your skills to identify undervalued properties, perform cost-efficient renovations, and build sweat equity.

We have had voucher tenants in two separate markets and have found them to be our top performers overall.

I would say it depends on how well the chunk of cash in your 401k is performing compared to the asset you are acquiring.

Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

@Nicholas Dillon If you sell a property and perform a 1031 exchange but do not reinvest all the proceeds, the leftover portion (called "boot") is subject to taxation.

I've noticed properties that are 2 bedrooms or less tend to perform better on this platform.