Area you are describing: Kailua on Oahu (
NOT Kailua-Kona on the Big Island)
Weather: Generally temperate with good tradewinds. It's green and lush in Kailua thanks to the rain which is regular enough to keep things growing but doesn't rain enough to be a nuisance.
Schools: A mix of private schools and public schools.
Private schools - Le Jardin, St. Anthony's, St. John Vianney, Redemption Academy, and a few other small private schools.
Public - Kailua Elementary, Ka'elepulu Elementary, Enchanted Lake Elementary, Kailua High, Kalaheo High.
There's also Lanikai Elementary which is a charter school.
Commute: Commuting from Kailua is generally very good. You have several ways of getting out of the area unlike other parts of the island which are two-way towns.
If you're going to the Leeward/Pearl Harbor side just take the H-3 highway. There's rarely any traffic. It's a quick 30 minutes from Kailua to Pearl Harbor/Salt Lake. The drive is scenic. When it rains you can see so many waterfalls over the Ko'olau Mountains.
If you're going to town you can take the Pali Highway. It took me 35-45 minutes during rush hour to get from Kailua to Downtown Honolulu.
There's also the Likelike Highway which you can take from Kaneohe to get to town.
You can also take the scenic route around Waimanalo and Hawaii Kai if you want another way to get to town. It takes much longer and it's worth it for those times you don't have to go anywhere in a hurry.
Food: There are many restaurants. You can find something to your liking. You can find Mexican, Thai, Italian, Chinese, "American", Korean, Japanese, fast food, plate lunch, etc. There are several bars including a biker bar. There's a mobile Indian restaurant that parks close to the Kailua Post Office. There's a really good NYC style deli (Brent's) near the Kailua Long's store. Thursday evenings from 5 pm to about 7 pm there is a decent Farmers' Market in the covered parking lot of the Kailua Long's store. You can find fresh veggies and fruits, organic items, local honey, sweets, and everything else.
Shopping: There are several large supermarkets - two Safeway stores, one Foodland, one Times, one Don Quijote (a Japanese store). There are two natural health food stores - Down to Earth which sells all sorts of organic and natural food items. It does not sell any meat or chicken though. There is also The Source which is I believe the oldest organic store on Oahu. They sell supplements, fruits, veggies, organic meats and eggs. A Whole Foods Store is scheduled to open in Kailua in 2010 or so.
You can find lots of small mom and pop type stores. There is an organic children's clothing store near the Kailua Long's. There's a Goodwill store and Salvation Army store for bargain hunters. The nearest mall, Windward Mall, is in Kaneohe which is about a 15 minute drive.
Air quality: Fabulous! Can't be better
Economy: Same as Honolulu. There is a hospital (Castle Medical Center), quite a number of small businesses, but you're not going to find too many urban jobs here. This is a suburban beach community.
Crime: Violent crime is not an issue. It's mostly burglery/property theft type crimes. However, Kailua feels safe compared to some other areas. There's a noticeable police presence in the community.
Housing prices: Pricey. $600,000+
It's a very desirable neighborhood and even older homes command high prices.
Good neighborhoods: I don't think there are any "bad" neighborhoods in Kailua. You have to drive the area to get a feel for the place but the neighborhoods all seem ok to me.
Some areas are older than other areas but it doesn't make them "bad" per se. For example, Coconut Grove on Oneawa area doesn't have good sidewalks compared to say Keolu Drive in Enchanted Lakes but the homes in the Keolu Drive area are "newer" compared to those in Coconut Grove.
Culture: Multicultural and diverse. You'll see Asians, Polynesians, White (haole), etc. Lots of churches. There are various organizations you can join like the YMCA, Rotary, Kailua Chamber of Commerce,This is a laidback beach town. It's pretty self-contained. You don't necessarily have to leave the area to find something to do.
Stuff to Do: Swim, surf, windsurf, hike, walk, bike, skateboard, golf, read, garden, exercise. You can go to Honolulu for any theater or musical event. The commute from Kailua is quite easy. Kailua has its own celebrations from block parties to the Fourth of July parade, Christmas Parade, to the I Love Kailua community parties. You can go to Windward Mall which has a large Border's Bookstore if you just want to enjoy a magazine and a coffee drink. You can go to two of the best beaches on Oahu - Lanikai and Kailua. Ka'elepulu Elementary has a HUGE playground. You could fit two schools in the grassy area that belongs to that school. Lots of room for kids to run around and play. Near the Kailua Library you find the City & County tennis courts, a junglegym for kids, and a swimming pool. There are several exercise facilities which offer everything from Pilates to Yoga.
Or you can just do nothing but people watch.
Other: I've lived in Hawaii for 30 years (showing my age here!
) and Kailua is my favorite place of all the places I've lived here.