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I have been to Vegas every month of the year. The best time for me (weatherwise) would be September/ late May-early June. The cheapest time- July, August, December between the ending of the rodeo and a few days before NYE. The most expensive time- no contest- NYE.
Any time of the year is a good time to visit Maui. If you're looking for the best deals on accommodations, spring and fall are the cheapest months to visit the island because demand is down. This means the island is less crowded as well, which is another benefit of visiting during these months.