Any creative ideas to buy a cash-flowing property in Hawaii?

[Prashanth Mannar]

'If' I have the opportunity to work remotely for a year, can I buy a Primary residence in Hawaii with a future goal of turning it into a Vacation home and/or STR? Why/why not?

[Lake Lutes]

Aloha from Oahu! Cashflow is a really tough goal to have on the islands, especially Oahu. However, it is definitely still possible. Of course, it's always going to depend on your mortgage which varies greatly depending on how the property was financed, but your best bet is probably going to be a property with multiple units, or a property with an "Ohana Unit" as we call them here in Hawaii. Think of these as "mother-in-law" units. Using a real current example on one of my investments, the home in the ~$750K range leaves me with an average mortgage of about~$3500. The 3/1 main home and has a 2/1 Ohana unit downstairs, renting for $2750 and $2000 respectively, cash flowing this property after all expenses are paid. To be fair, these kinds of deals have been much more difficult to come by in the last year and a half with the recent increase in demand. Nonetheless - you CAN cashflow on Oahu, you just have to be creative! Shoot me a DM if you'd like to discuss more.