Welcome to FT swright121 !!
Your questions are kinda open, so it will be hard for members here to give definitive advice. For what it is worth, Dec-Feb is the 'high season' in Phuket, and there are almost always heavy bookings for Xmas and NY well in advance for accommodation and flights. For the latter, it'll depend a lot on your preferred carrier.
We have all wrestled with this 'calculus' of when is best to book, and if there was a silver bullet answer, be sure the airlines would move to adjust!
Best advice will come from someone who has experience over a couple of seasons of similar travel from your origin (Nth America?). For me, I like to get in early and strike as soon as I see a decent fare, and I have a good idea of what that means to me from my origin. I recently purchased a QANTAS 'sale' fare from New Zealand to Bangkok return in Y late Feb for under $NZ 1200 ($US 900-ish) - this is a great fare. The sale was advertised for Aug-Nov, but the fares were loaded until Feb 13.
Hopefully someone can provide advice - and perhaps you can send a Private Message (PM) to FTer seanthepilot who lives in Phuket and travels between Nth America and Thailand.
Cheers, TK