Joining in on the fun...I will be there Oct 1-4, staying at DLH with the Gay Days rate. It will be me, DS8, my mom, my sister and my 3yo nephew. My sister hasn't been to DLR in 17 years and this will be my nephew's first trip. He is a massive Cars fan so he will go crazy for Cars Land! We also plan on doing a Halloween Party, a first for all of us, if the dates fall the way they did last year. Can't wait!
You should test out the headphones in the car or somewhere noisy before you use them on the plane. I say this because a lot of the new headphones for kids are volume limiting, which is safe for little ears but means the volume is often too low on noisy airplanes. We bought some new headphones for my son a few years ago and when we tried to use them on the plane he complained that he couldn't hear anything. I tried them too and he was right, so we had one very frustrated child on our hands during that flight! These are the ones we bought him when he was 2yo, he's now 8 and still uses them!
http://www.amazon.com/dp/B000M5GS7M/ref=psdc_12097479011_t1_B000MUXVZO
Also, SW doesn't always charge for wifi. I sometimes get an email the day before my flight telling me that I can use wifi on the plane. Follow their instructions and often times it ends up being free!
Those little playpacks are GREAT! Also, do not underestimate the power of a $1 pack of glow bracelets. Seriously, busting those out in the evenings has saved us on many occasions!