1. How easy has it been to make really good friends to socialize with - esp those in middle age territory? I am an introvert by nature though appear to be a regular social guy on the outside so I don't need constant friends and activities but would like a few core friends to hang out with, golf, etc. Hawaii seems to be notorious for outsiders to break into the established cliques for many obvious reasons.
2. I envision a typical day as one where I live in a place like Kailua, go play in the water, hike, or golf, then come home to catch up on the world, go get a dinner in town, chill out with the lady...and then do it over again the next day - and be perfectly content to pretty much do this for as long as the body is strong. For retirees in a relatively comfortable situation in a place like Oahu how much of daily life is 1) spontaneous, 2) doing things that you like over and over, or 3) dreadfully having no idea most days on how to entertain yourself even in Paradise?
1. Your first impression of local people is that they are very friendly. Most folks "drive with aloha" (put your turn signal on and someone will let you pull in front of them.) Meeting folks on the street or in a store, etc. you would thing making friends would be easy. BUT, making "close" friends of local folks can be very difficult. My take on it is that these local folks have been "burned" by getting close to us haole (generically, that means "foreigner.") Many haole get Rock Fever and return to the mainland or elsewhere - breaking a friendship in the process.
You can get lucky like we did. We met a haole married to a local girl in our first housing complex. We have remained friends ever since. In fact, we were invited to their extended Hawaiian-Chinese family luau for Christmas dinner with them last night.
The BEST way to meet people is through a traditional "association" of folks (church, club, service group, etc.) We have many friends through church, for instance. We also have many friends we have met through living in our "egg-crate" condo building. Full disclosure, the folks in the building are all haole like we are - from Cali. to ChiTown to Mass. etc.
So it is possible to make friends here. To some extent, YOU have to fit in, adopting as much of the culture as you can, being a student of what is appropriate, BEING a friend (just like anyplace else!), loving Hawaii, loving the ocean, loving the aina (land). If you have to fake it, you may not belong in Hawaii. Not everyone does - and there is no shame in deciding you don't belong ("Know thyself").
2. Heh, heh, a LOT of "what to do in Hawaii as a retiree" is just "what to do as a retiree." If, like us, you come from the middle of the mainland, you can picture Hawaii as "just like home" except it's always summer, you are 1 to 10 miles from the ocean instead of 2000 miles, your back yard is up against a mountain instead of 1000 miles from mountains, you can virtually pick the weather you like by what part of an island you live on (no winter, unless you pick Big Island or Maui).
You can pick your "era" by the Island you choose (Molokai is 1950's, Big Island is 1960's, Kauai is 1970's, Maui is 1980's/90's and Oahu is about 5 years behind Cali.
So for us, we have "planned" events (revolving around friends, church, etc.) at least 4-5 days of every week. We also DO spontaneous - especially eating out or going to the beach, learning a new neighborhood, cruising the real-estate open houses, etc. I do like to play on the computer and she likes to do crafts, cross-words, read. I can't recall being bored since the last time I was snowed in back on the mainland.
IF you fit the life-style here (and it is varied, so difficult to define) you can be as happy or more happy than on the mainland. IF you bring "baggage" with you (Hawaii most likely will not cure old hurts, couple issues, money problems, etc.) you can be just as miserable as anyplace else. Always remember that where ever you live, YOU are there. I just think of Hawaii as "home" but more-so.
Hope this helps. Best advice I have to offer (and recall that it is FREE advice): Rent for a year, maybe move around Islands or at least within an Island. Sample everything. Immerse yourself in the culture. Keep your expectations in check. Go with the Island flow. Know yourself.
In all of this, remember that YMMV.