As far as booking goes...

I'm not sure that two years in advance of peak season (true peak seems to refer to the time period encompassing the North American Christmas and New Year's holidays) is too far to start thinking about things. Booking? Yeah. Thinking? No.

My wife and I are planning to spend a good chunk of time at Starwood properties in SE Asia at the end of the year (mid-Dec '10 through mid-Jan '11). So far, here's what we're planning, with a 4-5 night stay at each property.

1. LM BKK
2. LM Chiang Mai
3. Sheraton Krabi
4. Somewhere on Ko Phi Phi (no SPG properties there)
5. Sheraton Kuala Lumpur
6. Sheraton Sengiggi Beach (Lombok, Indonesia)
7. Laguna Resort & Spa (Nusa Dua, Indonesia)

What I've found is that if you want to book the beach hotels right during peak season, you need to jump on them ASAP. LM Khao Lak I think was available for C&P redemption but isn't anymore. We grabbed Krabi at the C&P rate, but don't see it available anymore. LM BKK and LM CM seem to have good availability during the front part of our trip, as does the Sheraton Sengiggi when we get down there in early January. I couldn't find C&P availability at the Laguna until Jan 7. (I didn't try any dates in December.)

So... I'd think now for the next few months, and then when the rates get loaded at the end of 2010/early 2011 for your stays, be ready to pull the trigger. The good news is that award bookings don't come with any change fees, so you can be ready to go if you find the availability.