Hey mate, can offer some advice for you
Fly into Manila, jump on a Seaair flight to Caticlan, taxi to Caticlan jetty port then boat across to the island. Its about 2-300p to get a bike from the jetty port on Boracay into Bulabog beach where the wind is.
Bulabog offers accommodation but it might be a bit pricey if you are alone, I think we paid $1000p for 1 week in a basic hotel unit around 200m walk to the beach, i'm sure you can get it cheaper if you stay longer.
I'm pretty sure the Amihan season (the best for kiting on Bulabog) is between Sept-Mar. So December it would be heating up - i'd personally leave it until Jan, but its up to your time schedule.
Winds blow from around 7am till 4pm, 15-25kts EVERY day when I was there in '09. In '10 it was a LOT windier (30kts), followed by days of no wind at all. I'm sure it was because of La Nina though, you should be ok this year.
In terms of crowding - yup it is pretty packed. If you manage to get the right tides and can get out before 10am you will definately have a couple of hours to yourself/minimal people. But usually after 10am its a bit of a maze. There are other areas to kite further south of the island, you can also arrange island hopping. Speak to Glen @ Ocean Addicts, we did the Seco safari with his crew in '09. F*kn amazing. Flat water, pumping wind, middle of nowhere, just you and your buds.
White beach (other side) is the 'party' beach with bars, clubs, cheap & nasty cocktails and drunk euro's etc. 10-15 min walk from Bulabog. Filo people are great and will help you out, but of course as per usual Asia tourist location there is a charge with everything. You can barter most services down a bit - but its asia, so still cheap as.
Have fun and dont get drunk and lose your ID, wallet, visa card, camera....like I did. Take cash only everywhere!