@Jon Kim Your property qualifies for cost segregation and bonus depreciation regardless of it's used for short term or long term renting.

This shift underscores the advantages of private money’s agility and long-term outlook, unencumbered by the need for committee approvals or short-term returns.Recently, large funds have been facing challenges due to immobile private equity assets (worth $3.2 trillion) as a result of reduced dealmaking and a slower IPO market leading to delayed investor returns.Meanwhile, state and municipal governments have witnessed a remarkable surge in borrowing to fund affordable housing initiatives totaling nearly $9 billion.

We would like our portfolio to be primarily long-term rentals with short term rentals filling the gaps.

So, I suggest before you buy something else you need to figure that out.Life is short for "senior investors" like us, so live your best life and buy wherever it makes you happy. 

. :)   The area has definitely been changing the short time I've been in.

True, However if you evict and you don't have it, they'll give you a short time to get the clearance, then they'll put an injunction on you, Legally preventing you from re-renting the property.

I am looking into renting to listing on Airbnb and furnish finder for my mid term rental since Honolulu is not really short term rental friendly outside of the tourist areas.Would like to hear others experience doing mid term rentals in Oahu.

I would not count on short term appreciation to be great.Negative cash flow can get old fast   Especially when large cap expenses occur.  

Looking forward to learning more of the processes and expanding into a few short to medium term rentals.  

Submit offers and negotiate terms with sellers, being prepared to walk away if the deal doesn't meet your requirements.