To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

I think you'll find no one is going to care so long as it's not sandpaper or thin enough to read through.  

There is nothing about how long you need to occupy the property for.So unless our lender puts a demand on us I see no problems legally in occupying each property for any amount of time to fulfill the requirement, then rinse and repeating this process up to our full entitlements, so long as the lender is willing to keep giving us loans.

I don't plan to ever move the property, and I want to keep it as a rental as long as possible.Thank you

There's no wrong way, as long as it makes sense for YOU.

It doesn't matter the company you work for as long as you are part of the real estate industry. 

As long as you're prepared to be a landlord and live next to your tenant for at least a year, house hacking is a great way to get started.

Who are we to say how many places they can rent at once as long as their income meets your requirements?

So, as long as the charge is reasonable I would charge it.

Hi Colleen,As long as both of the units are fully rented, there should be no issue getting another DSCR loan.