My final question is the Disney Dining Plan, is it worth it for a 2 week holiday?
Mickey's Not So Scary Halloween Party also takes place on selected nights in October in the Magic Kingdom.
Additionally, Halloween Horror Nights at Universal Studios Orlando and Howl-O-Scream at Busch Gardens Tampa occur nightly in October.
In general, October is a great time to visit (some would argue that mid-November can be even better because many of the parks already have their Christmas decorations up). The crowds are generally pretty manageable, and the weather is far more tollerable than mid-summer (low to mid 80's and low probability of afternoon T-Storms).
We almost always go to Orlando in October, mostly because of the EPCOT F&W Festival, and will be there at the end of October this year.
The current Free Dining promotion is a little tricky. You need to book at an on-site resort, and the level of the Dining Plan is dependant upon the level of resort you reserve. Value resort guests receive the Disney Quick Service Dining Plan, which includes two (2) counter service meals and one (1) snack per guest per night. If you maximize the value (eat the most expensive meals at the most expensive counter service restaurants at WDW), you're probably looking at @$30 per night of savings. However, if you are unable to maximize your Dining Plan, you could only get as little as @$20 in value per night even if you use every credit. Sometimes the Dining Plan can be a burdon if you cannot keep a schedule or are a picky eater.
Guests booking at moderate and deluxe resorts get the standard Disney Dining Plan, which includes one (1) counter service meal, one (1) table service meal, and one (1) snack for each guest per night. Again, depending on how you use your credits, you could probably get as much as $60 of value per night on this plan. For us, we have booked at Port Orleans French Quarter, and with the Dining Plan, will probably cut our nightly hotel costs to about $20-30 per night by maximizing our Free Dining Plan by booking charater meals and certain dining experiences.
Also, in the past, Disney Dining Plan snack credits have been accepted for most food items sold at the EPCOT Food and Wine kiosks in the World Showcase, but there's no guarantee. A snack credit could be worth as much as $9 if you get the New England Lobster Roll at F&W, or as little as $1 if you get a bag of chips or a piece of fruit from a standard eatery/c-store.
FWIW, the resorts appear to be pretty full already for most of the second half of October (including the new Art of Animation, which isn't eligible for the free dining promotion). The free dining promotion is only eligible for certain rooms and cannot be combined with other discounts or offers. Again, it all depends on how you use the Free Dining if it's worth it to you. We defeinitely maximize the value. 2 years ago, we effectively made our resort (Pop Century) @$14/night, but back in 2010, the quick service plan included two (2) snacks per day. Here's my analysis of the Disney Dining Plan in 2010...http://www.themeparkinsider.com/news/response.cfm?ID=945507604
If you're there, don't miss Halloween Horror Nights.
Although we didn't have tickets for special event and we still enjoyed the Food and Wine festival a lot!
October is the best time in my opinion! I go every year for Halloween Horror Nights at Universal! The event is crowded and often overwhelming but is also great fun, love the scare zones and the haunted houses (the shows like Bill and Ted's have become pretty lame last few times, but hoping they get better soon)and I love just sitting in the park and listening to all the fun stuff happening! Universal has worked on making the event better and better each year, they still have issues such as too many express passers holding up the regular lines and I think they should devote more time to taking care of the annual passholders then what they do!
Also last year I went to Disney one night for the Scary Mickey Halloween parade which was fun, but not nearly as good as universal's halloween party!
If you have not been to Halloween horror Nights, I would suggest giving it a try!
Walt Disney World
Tokyo Disney Resort