Paradises the world over are littered with stories of people who packed up their hum-drum lives and moved to paradise only to discover it was quite different from the post cards. Certainly a good rule of thumb for any move — “Rent first” — is doubly important when moving to costly locales you’ve not spent enough time in to really understand whether you’d be happy there.
Before I purchased my second home, I’d spent many months over several years renting in the building before the stars aligned and I purchased. If your second home will ultimately be your post-retirement home, you owe it to yourself to thoroughly investigate.
These cautions bring me to 61-753 Papailoa Road. Far from a typical rental at $30,000 per month, it’s the most expensive home for lease on the island. But it’s a beachfront single-family home located on the famed North Shore of Oahu … and you pay for that. The home is only available from December through March (when I assume the owners are off elsewhere). It’s also month-to-month, so don’t be pestering the agent (Kimo Smigielski of Sandwich Isles Realty) with your 2-day rental requests.