Right now its slim pickings in real estate for properties that will cash flow or see any significant appreciation. of course they are always out there but a lot harder to find.The other question is why do you want to continue to grow?

@Marcus Stokes, house flipping is a full-time business operation, even with current market conditions.

•Operating Expenses Account: For monthly expenses.

Personally, if your market tends toward the former condition (better/normal appreciation) I think it's a fairly safe deal looking at the long term, assuming infrastructure around you continues to support the idea of renting it.

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.  

Are you intentionally looking to outsource the management and day to day operations to a management company versus self-managing? 

An entity that operates hundreds or thousands of apartment units has far less concentration risk than an owner of a few rental homes, whose tenants may all be impacted by COVID-19.Do you think Portland’s ten-year trend of positive economic growth for landlords will continue, or will it flatten out, possibly even declining in the wake of COVID-19?

Take your time to clarify your goals, and be ready to continually learn and network along the way.Remember, each step you take is a valuable experience that brings you closer to success.

The buyer would need to show solid financials also of course (good credit, experience operating rentals, proof of funds for down payment and adequate reserves to cover any unexpected cap ex).

I've lifted the ban, you are free to continue to send messages.