I agree that anytime you go is a magical time

, but if swimming is one of the things you want to do, I would guess the sooner the better (Not really sure of temps in Oct/Nov). The resort choice depends on what you are looking to spend and what theme your family likes. I have never stayed at the value resorts so I can not tell you about those (I am sure that someone on this board can though). I have heard wonderful things about them though! The Moderate's are very nice..our favorite is the POR. We tried Corondao Springs but its theme was just not for our family (we ended back up at the POR after only one night). We have walked through CB and thought it was pretty cool. My best friend stayed there with her family one year and they loved it. Never stayed at the POFQ, it looks really nice, but its theme is not what we like. We like the rustic feeling of the POR Alligator Bayou section

. We are trying the Poly this year

, we have been there a few times to walk around, but never stayed there. It is a very lovely resort. We stayed at the GF on our honeymoon, but that was quite some time ago, but we absolutely loved it

!! We would like to stay there again.
I would say that 5-7 nights would allow you a good amount of time to see quite a bit...not everything, but plenty. Definately come back to the resort for afternoon breaks (nap time, swimming, etc.). We have done this every year with our kids and it really helped with getting in a few more evening hours. We would come back, have a quick snack, change into our bathing suits and go to the pool for an hour or so and then come back and have the kids take a nap or lay down for quiet time (the older ones would lay there so the younger could fall asleep). Sometimes we would all end up taking naps

, we get so worn out with all that we do and the heat!!
I can not help you with the childcare question, we have never needed childcare at WDW (I am not a very trusting person when it comes to my children...I had a bad childhood

).
Let's see, things not to miss....my girls all loved the "It's a small world" ride at MK even when they were only a few months old and they still love it. Country Bear Jamboree at MK. Toon Town Hall for character meets at MK (If he is not afraid of characters). My daughter was 2 1/2 last year and she loved Goofy's Barnstormer at MK. The Jungle Cruise at MK. Muppets 3D at DS. Playhouse Disney at DS. There is plenty of things for a 2 year old to enjoy at Disney

I could go on forever!! I would also have a few character meals if, again, he is not afraid of them. Chef Mickey's at the Contemporary Resort is a great one (they have Mickey, Minnie, Goofy, Donald, Chip and Dale). Crystal Palace in MK (They have Winnie the Pooh characters). There are plenty of others, but those two are our favorites.
Welcome to the DIS, good luck and happy planning!!
