I was at WDW in mid January in 2007 and 2008. You can read more detail HERE about my experience with crowds and weather. I think you'll find the crowds to be moderate to low. The weather could be almost anything. The average daily highs in January are in the low 70s. But in any given year, or even within a single visit, you could experience anything from mid-80s to mid-40s. Be sure to check weather.com before you go for an up to the minute forecast and bring lots of layers. One other thing to tell you about is that Disney Marathon weekend is January 8-11. I don't think this will have any real impact on your trip, as many of the runners come for just the weekend. You will see lots of guests wearing Marathon shirts, etc. I have found it very interesting to talk with them about their experiences during the race. I like to live vicariously through someone else's exercise :-)
As far as making your meal reservations goes, I would NOT NOT NOT wait until you book your room. You can always change or cancel reservations, but you cannot make them once the slots are full. I wouldn't be at all surprised to hear that Cinderella's Royal Table is already completely booked for the week of your visit. Many of the other character meals will have only very early or very late seating left. For character meals, or signature dining, MAKE THE RESERVATIONS NOW. If it turns out that your trip doesn't work, just cancel the reservations. I'll be at WDW for MLK weekend in 2009 too. Stop and say hi if you see me!
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