Short term it is difficult to make the numbers work, the cost of new construction and the time it takes to zone-plan-build are usually the main reasons why private investors stay clear.

I plan to live in the multi-family for a year then move out and rent the unit.

A tax advisor specializing in real estate can help you navigate deductions, plan for 1031 exchanges, and ensure compliance with ever-changing regulations.

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

Congratulations to you for setting yourself a goal and having a plan in place to execute it. 

I would both buy a property to get your feet wet and at the same time make a plan to scale.  

@Jerry Zigounakisi'd pick a market close to you, or one you have strong ties in, rather than trying to get to one via math.can you invest where you live, or 1-2 hours from where you live, or where you like to vacation, or where you went to college, or where you plan to move someday?

They are holding the proceeds from my sale and I am planning to buy a couple of DSTs shortly.

Happy you joined the party.. how soon do you plan to start crunching numbers on a potential deal?

Someone planning on stealing anything of worth is going to do it while you are gone.