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Hi Bloke, welcome to the board. For basic questions you can generally find answers by using the search function and finding previous threads on the same subject.
On your specific questions I would say:
Depends how much of a party you want, December will be busy and New Year will be mental. Up to you.
Book flights sooner rather than later, and if you are going at that time of year then booking a hotel before you arrive would be a smart move.
Have a look in the Accommodation thread for hotel advice.
Most flights you find will be via Bangkok, it's no big deal.
Have a great trip.
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