The rents listed all over the bay area (for 1br) sort of knocked me out. I know the area is popular, but at least there is a fair amount of land around on which to build more housing. On Oahu, we don't get any more land (IIRC 597 Sq Mi total). That fact and the "paradise" tax would have made me think our rents would be closer to the Bay Area rents. We own, but our apartment would rent for $2500 or less (some for as low as $2100 - depending on amenities and view, e.g., the Pacific.) We have 1100 SF and 2br 2ba with a fantastic view. THE BUS service is relatively inexpensive and virtually ubiquitous on the Island so, though we own two cars, we could live without them - especially as retirees.
Bad as Oahu rents are, it seems there are places much worse - especially if you want to live close to the action (heh, heh, we're about 30 miles from the farthest point we could drive to - and I don't want to drive there (again.) Many rents are actually a "bargain" compared to the actual price if one were to buy. I think that tends to be fairly common when average housing cost is in the $700K range or higher (our condo was considerably less than that.)
But back to the OP's question. My suggestion is to get lucky and I'm only half joking, here. We did when we bought 30 years ago in anticipation of retirement from the mainland. We bought WITH a couple of tenants and kept them for 20 years. Then we hired a real estate management person who got us more rent and really looked after our investment for us. (DW and I often joked that our agent would never have rented to US!) We DID do serious research on her (one person). We figured that was much better than a big "firm" - also from what we heard from other folks, though I'm sure there are some great management companies. With one agent, there is one person to deal with and one person to "blame" if the ball is dropped. We could have never made the move had we not bought in when we did. Prices sky rocketed at the same time mainland (well, the heartland) seemed to just chug along, RE price-wise. It's a big decision and I emphasize that we were very LUCKY (or blessed, depending upon your view of life.) So, more than ever YMMV and good luck.
Ko'olau's Law -
Anything which can be used can be misused. Anything which can be misused will be.