I think we'll be there before you. I'll be hitting WDW from 29 Sep - 7 Oct. Your ticker suggests that you're there late October.
Yeah, you two aren't overlapping either. If you had both been there at the same time I may well have HAD to come down.
Wow, you are super planner! Look at all those pros & cons!!!!
Well my vote is November. But then... that's because- duh- November rocks! Cuz I'm in the parks. Ha!
Yeah, I should've put you in the November + column: Meet Tinker326 and her family! Well, I couldn't really, as I did all that planning prior to "meeting" you. Always look forward to meeting DISers though
We've done this particular week in November (the week prior to Thanksgivingish) twice & out of all our trips (we've done Jan, Feb, March, May, June, October, Nov & Dec) it's always been our absolute favorite.
Great weather. Low crowds. In my mind, you can't beat it. It's why I pull my kids from school for it- although SO SAD this will be the last year I can really get away with doing that with DD going into 6th.
I agree, we've done April, May, August, September, October, November and December, and it really is my favorite week that we've been, though we've done 3 weeks in late October and they've been pretty spectacular too!
Our same issue, DD will be in 5th grade this year, so once she reaches middle school I will not want to pull her out. (My parents always pulled me out for vacations right through high school, but I was an excellent student. DD isn't there yet.)
I had heard that there are November park hours floating around. I'm going to research at lunch today & starting working on tentative ADRS!
Oh, you made me check my "go-to" site:
http://www.easywdw.com/ and they had them! Go there for the link.
I always use the previous years operating hours for my initial plan, and then work from there when the schedule is updated. It is usually about 95 % unchanged. They then throw a few wrenches in the works as we go, as often they put some change up a month or so before leaving. That website Is Really good about keeping the schedule up to date. They also have free recommended parks and crowd levels - unlike the old Touring plans / Unofficial Guide who charge for it.
I am still debating the Christmas Party too. Like you we did it several years ago and were NOT wow'd by it (love the Halloween one ironically). It didn't seem there was much 'extra' offering for the high price. So I'm still on the fence about this..... the late night really cuts into the next day touring as well.
Let the planning commence! Woot.
I biggest complaint about the
MNSSHP was the CROWDS. It was far and away the most crowded thing we attended that week. We waited in HUGE lines to meet some characters, and only got to meet 3 or 4 groups of characters. We also had to stake out a spot at least 45 minutes early for the LATE parade. We only had time for like 3 rides the whole time, DD was cranky and tired. It was OK, but probably one of the "worst" times I've had in a Disney park. ("Worst" being relative, we still had a lot of fun.)
As far as the Christmas stuff, we've seen it all. Starting the day after the last Christmas party, usually the Saturday before Christmas, they do the parade and all the shows for "free". Our December of 2009 trip overlapped with the start of Christmas season, so we were able to catch it then.
However, DD at Christmas this year says she doesn't remember seeing the parade. DW said that she would pay so we would go to the Christmas party. I said the only way I would go is (1) it has to be lower crowds and (2) we're not going to spend any time waiting in lines to see characters since DD doesn't want to anyways. If we do it, we must take advantage of the short lines for top attractions and then also see the parade and fireworks up close (We've seen Christmas wishes twice from the top of the Contemporary.)
From the looks of it, the choices are 11/8 (Fri), 11/11 (Mon), 11/14 (Thurs), 11/15 (Fri). I beleive Friday the 8th is the first party of the season, so we won't do that one. I'm thinking the Monday party so early in the season should be pretty low crowds, the locals will mostly wait until Thursday. The crazed Disney fans will go after the first one. By doing Monday, we're going to leave Tuesday as our "off" day (resort day).
We're only going to do the party if they actually have free dining, but I think that'll be our date.
Well, time to go and update our spreadsheet! (or perhaps I should be doing actual work.)
Of course, it would be great to meet up if our trips overlap, but you gotta do what's best for your family, and it sounds like November is it. I think planning both trips and deciding when it gets closer is still a great idea though! 
Although, I'm still not certain I will make the entire 13.1 miles at the rate I'm going with training (um. horribly. but my cookie that I'm eating instead of running is good!) 
