I lived on Oahu for three years. Yes, there is humidity but the pretty much constant trade winds will mitigate a lot of that.

I would opt for air conditioning in a hotel when possible.

In two weeks IMO you could certainly do three islands; obviously a great deal depends on what you want to actually do once you arrive.

I've been to Hawaii several times and find it to be the most comfortable tropical destination I've been as far as temp and humidity goes. It's just about perfect. I in the two island crowd also. If you don't really want a "city" feel, id suggest maybe just spending a couple of days in the Waikiki area and then driving to the north shore and staying a few days there. I love Waikiki and could easily spend a week there but I do realize that's not for everyone.

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Actually if you're able to fly non-stop from island to island (some you can, some you can't), I find it doesn't take more than half-day at most. Generally, we can be at the pool/beach at our new hotel by lunchtime.

As for the Waikiki debate, it is developed, meaning the beach is lined with hotels, restaurants and shops. To some that means it's overdeveloped, to others (myself included), its a pleasant beach city. You don't go to Waikiki for nature (that's what Kauai is for LOL), but it's an enjoyable spot in its own right. Like Suze, I don't always (in fact, ever) want to be totally isolated, so if I can be sitting on the deck sipping a nice drink, with a tropical breeze blowing, I don't care if there are 20 or 30 or more hotels filled with people doing the same thing (although waiting for a table at a popular restaurant can get annoying)

I really liked our stay in Waikiki beach. It is a fun city on the beach and has so much to do. We stayed at the Hilton Hawaiian Village on our last trip which is a large scale resort. We have stayed at the Halekulani in the past (small beautiful, but expensive hotel with some great history). We were there on a business trip. There are many great places to stay with different prices.
I did read about a resort on the north shore called Turtle Bay. I have not stayed here, but looked into it for our last trip. We wound up staying in Waikiki and then moving islands.

I love Oahu! I especially love Waikiki because I am a New Yorker who is used to walking everywhere an I can do that in Waikiki. LOL. But I do think the best eats are found outside of Waikiki. And I love the Halekulani and Royal Hawaiian. I want to vacation wherever Don Draper does...mai tai in hand.

I just spent almost 2 weeks on Maui, and although it was a fantastic vacay, I do also miss the conveniences of Honoululu where most things are centrally located. We had to drive everywhere in Maui - although when we were at a condo we ate in a few times which was nice.

So glad you are going, nelsonian, and I think your 3 island plan is a good one!