Thanks for all of the replies!!
His birthday is at the end of October, the 23rd. So we'd probably either go the week before or the week after...or into November. Nothing is set in stone yet.
The walks to the park from the resort hotels aren't that long at all, then? Nice! Sounds like it might be faster to walk than to utilize the monorail fi you're trying to get to the park/hotel quickly.
The package I'm looking at ( through Costco) includes the character breakfast. If it didn't, we probably wouldn't pay extra to do it. At least not this trip.
The getawaytoday.com deals list $350 in coupons. Does anyone know what the coupons are? Are they something useful?
I'm not worried about some of the rides being closed for refurbishment, at least not right now. I'd prefer to go when the crowds are lighter anyhow. Same thing with the Halloween party. I can same money for extra souvenirs and whatnot by skipping the party. Logan will not know the difference either way!
When does the park typically dress up for Halloween/Christmas? As long as the haunted mansion and pirates are open, that's all I care about, lol!
Also, how long is the 60th celebration on for? is it over at the end of this year, or is it going to run for a full year? I want to go during the celebration, so I might even push the trip out to January if I can score better prices!
Thanks!!
To answer your question about when the park dresses up for Halloween and Christmas... I will explain (those are my main niches here on the board, so when someone mentions Halloween or Christmas, I hear the call and come running!

).
In a normal year, Halloween Time would probably start on Friday of the week after Labor Day week. Last year it started on September 12th, but Labor Day was on September 1st. This year Labor Day is on 9/7, and I think that 9/11 might be too early for a Halloween Time start date. Also, we don't know if the events of the 60th will in any way interfere with Halloween Time or the holidays.
Halloween Time will inevitably start by or before 9/18, with a best guess of somewhere between 9/12 - 9/15 (because of the season's popularity). Before the official start date, pumpkins will begin appearing over the Disneyland turnstiles and assorted Halloween/Fall-ish things will start to pop up in the shops on Main Street.
Haunted Mansion Holiday and Space Mountain Ghost Galaxy will open on the first day of Halloween Time in September (whatever that date turns out to be). Haunted Mansion Holiday will remain open all through Halloween Time and the Holiday season, into early January of 2016. Space Mountain Ghost Galaxy will probably close after Sunday, 11/1, I am guessing. The Halloween Carnival at Big Thunder Ranch will close right after Halloween Time ends to get its Holiday season overlay, for which it will become the Jingle Jangle Jamboree in mid-November.
Mickey's Halloween Party would usually begin on the last Friday in September, and then last through the whole month of October (every Friday, most Tuesdays and some other nights thrown in). This year we don't know if it is starting earlier or later than usual.
The Holiday season is a much more involved, extensive effort around the entirety of Disneyland Resort. Whereas Halloween Time mainly takes place in Disneyland, the Holiday season involves both parks, all 3 hotels and Downtown Disney. So, even before Halloween Time ends, there will be traces of holiday décor sneaking into certain lands. Everything has to be set up by the first or second weekend in November.
Most holiday entertainment and ride overlays (such as It's a Small World Holiday) will soft open before Veterans Day or by Veterans Day weekend, and before the holiday season officially starts, but some things won't begin until the official start or after. The holiday season will officially start after Veterans Day. I am guessing that this year, the holidays will officially begin somewhere between 11/12 and 11/16.
The 3 Disney hotels begin to get their decorations about 9 days before Thanksgiving, so around 11/17 this year, and then the gingerbread house in the Grand Californian Hotel lobby should be fully installed by Thanksgiving. The ice rink and Winter Village in Downtown Disney will probably be open by the weekend of 11/13-11/15, or a couple of days later.
The new shows for the 60th are supposed to last at least through the end of this year, but we don't know how far into 2016 they will extend.