First Time Investor - Looking to buy Waikiki Vacation Rental

[Antoinio Arnold]

I’m buying my first home, a condo in Waikiki. When I depart Hawaii in about 3 years, I plan to keep the place as an investment property. I have a choice between a cheaper place ($330,000) that would only be suitable for long term rentals, or a more expensive place ($440,000) I could use for 30 day or more vacation rentals or long term.

Can’t do anything less than 30 days though due to HOAs. So I’m looking for info on the 30 day+ rental market in Hawaii. I want to figure out if the potential cash from using the more expensive property for vacation rentals would offset the higher cost eventually or at all. Help? Thanks!