If you choose to move forward, I recommend having a backup plan in case Hawaii outright bans STR.

It depends on a lot of factors; primarily the local jurisdiction rules that may limit lease changes (in Portland/Oregon rent, security deposit, screening fees, an no-cause evictions are heavily regulated).

@Michael DartenMichael,Let me know who choose and how it works out, I wouldn’t mind having a backup.

Hi Kmsuea, it all depends on your commitment to actively looking for and purchasing a property. 

And good luck to whatever you choose to do.

Depending on your investment horizon that may matter or it may not.

new construction gets valued at a way higher premium. this is a false statement. new construction will always beat existing Very market dependent.

Choose my own real estate agent

Because we are dependant, for the most part, on word of mouth recommendations it is vital that our recommendations are valid. 

The property itself should bring in revenue ( even if you choose not to live in one side) and generally a bank will accept a portion of that rental income into the calculation.