I hear you on the cold weather, but is that your primary criteria? The reason I ask is that spouse and I moved here somewhat reluctantly but then came to love living here. When we returned to the Mainland (military transfer) we expected to "get over Hawaii" within a few years but every time we returned here it felt like coming home. In addition to the weather we love the multicultural society, the beach lifestyle, and the easier access to Asian travel.
However many people move here for the weather and immediately encounter other obstacles: insularity against short-timers & snowbirds, lack of familiar Mainland cultures, lack of seasons, lack of access to impromptu "pick up and go" travel, five-hour flights to the Mainland, language/culture barriers, expensive Mainland foods, and even loneliness. Some object to "strange foods" or $4/gal milk. Living in close proximity to critters has been a problem for others. Vog, hurricanes, and earthquake are also unpleasant surprises. Rock fever is endemic among military here (although perhaps just as many others love the lifestyle) and many eventually decide that there are other Mainland locations with adequate weather. Even retirees here struggle with caring for aging Mainland family or wanting to be closer to their (Mainland) grandkids. If you're "commuting" to the Mainland even 3-4x/year, those five-hour flights get old in a hurry.
In other words you'd hate to move here, buy a place, and then spend the next couple years realizing that it's been a mistake.
Of course if you're a diehard surfer then never mind! None of that other lifestyle stuff matters because you'll be spending most of your time on the beach and in the water. Just figure out your favorite breaks and then pick any property within a 30-minute drive.
... but with real estate the way it is, I'm starting to think we should purchase now in anticipation for the future.
I'm not sure there's any rush. In the next 5-8 years you could still find a bargain. Over the last two decades our rental home has appreciated at almost exactly the rate of inflation. However that started at $277K (1989), zoomed to $425K in one year, then spent the next decade cratering to about, oh, $277K in 2000, spent the last decade getting up to $600K, and has since retrenched to about $550K. I wouldn't be surprised by flat values for another five years. A better bet would be to find 2-3 areas where you'd like to live and then buy a place that's been neglected/abused and is selling well below market.
The problem is that your current location renders you essentially clueless about the details of the Hawaii real estate market. You could spend a lot of time on the web to get more info but you'd still need to spend a few hours at open houses. You could work with a realtor, but they've seen a bezillion Mainland customers and know exactly how to put you through the high-pressure sales meatgrinder. They'd whip you into a frenzy of artificial urgency and you'd overpay. You should consult DangerMouse about her run with realtors before her memory of the experience fades to a warm hazy glow... and overall she had a pretty good experience.
So you might want to casually keep an eye out for areas where you wouldn't mind living, and then rent for a year or three. During that time you could get to know the neighborhoods, visit a few open houses every month, get to know the realtors, and eventually swoop down on a bargain.
... and want low maintenance, lock and leave condo.
... but think we'd like to look on Oahu.
... would not want to live in the city.
Don't really want the place to be in a total tourist setting
Our price range would be 400-600K, prefer close to water but would not rule out upcountry locations with views....
Ideal living would be without need for a car, but I'm not sure that is possible unless in Waikiki/Honolulu.
Well, you've certainly narrowed down the options. Unfortunately you may end up having to make compromises.
If you want to be "near" but not "in" Honolulu then you're looking at pretty expensive stuff around the periphery-- Kahala, Diamond Head, Hawaii Kai, Manoa. Farther west toward Kaimuki has good neighborhoods among the "other", but you'd be looking mostly at high-rise living. You could do a lot with Da Bus but you'd still want a car to haul your longboard to the break.
If Honolulu is important but you don't mind commuting then you could try the Pearl Harbor area: Red Hill, Foster's Village, Aiea Heights, Salt Lake. Condos vary dramatically in price but are especially thick on the ground around Aiea/Kaahumanu Ave, Pearl Loop, and Salt Lake. You'd go into town for surf (Ala Moana) or out toward Ewa.
If you don't need to be tied to Honolulu then you have more options. Kapolei, Ewa Beach, & Makakilo have more condos/townhomes and the south shore surfing is excellent (White Plains Beach at Kalealoa). There are cheap/decent condos in Makaha, which also has excellent surf of course, but there's a strong locals-only vibe on the breaks there and kooks would be actively persecuted. You'd find cheaper real estate but not so many choices, and the HOA fees could still easily be $500/month.
Another semi-urban option would be Kailua. It ain't cheap and it doesn't have as many good surf breaks but it's big for kayaking, stand-up paddleboarding, and windsurfing/kitesurfing. But if you're going to live up there then you definitely don't want to be tied to Honolulu.
If you don't mind being a good 60-90 minutes outside of Honolulu then you could look at the Haleiwa area of the North Shore. You'd be able to buy a condo or home (for big bucks) and rent it out at ridiculously high prices during the winter surf season. The problem is that you might want to actually be living there during the winter surf season.
If you haven't already then I strongly recommend that you sign up on HawaiiThreads.com and re-post your questions there. You'll get a whole new set of answers (some of which will overlap this thread's answers). Read about others there who've tried to move to Hawaii, and you also may discover a few obstacles that you hadn't thought of. While you're at it, start reading
the Star-Advertiser and look at their real-estate articles.
In conclusion, I think your best option is to spend your visits here learning the neighborhoods and going to Sunday-afternoon open houses. Don't engage with a realtor, just familiarize yourselves with the local areas and the real-estate standards. When you move here you should rent for a year or two in your chosen area to see if you're acculturating while you're keeping an eye out for bargains. By then you might not even need/want a realtor.
I recommend Franko's Maps for figuring out the names/locations of the surf breaks.
This guide is focused on surfing but they offer other guides for diving and for general Oahu activities.