Raised on east side of Oahu but also lived on Big Island and Maui, and also have family on Kauaʻi, and plenty good friends on Molokaʻi and Lanaʻi. That being said I try to get away from urbanized crowded Oʻahu as every chance I get. One thing nice about Oʻahu are itʻs beaches and itʻs mountains. Haleʻakalā and Mauna Kea may be taller but the beauty of the Koʻolau mountains especially the water carved cliffs of Windward Oʻahu cannot be matched. Waikīkī is a fake manmade beach but hard to beat the beauty of Kailua, Waimanalo, and Makaha beaches. Beam about a million people off the island and Oʻahu would be perfect. Favorite drive is along the coast between Lāʻie and Kahaluʻu. Whale season right now so you may get a chance to see them. Allot of great hiking trails, and eateries. Let me know if you need suggestions on these.
Aloha a hui hou, Ahnko