Hi Lindsey. Overall, early to mid-October based upon my experience is generally a good time to visit from a crowd perspective. As for the weather, you noted the nice weather of early November from your last visit. That also happens to be one of my favorite times here in Florida where I live. Comparably, I believe you will find the October weather to be a bit warmer. The other factor you should consider is the higher potential for rain. During August, September and early parts of October, the likelihood of rain showers daily is higher than other times of the year.
As for the week of Halloween, I did visit during this week two years ago and was pleasantly surprised about the crowds. In fact, Disney lists this week for 2008 as one of the better times to visit. While you are considering a 2010 visit, this calendar may help pinpoint pockets of time that are generally better to visit based upon crowds, weather and cost. Hope this helps!
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