Wow, I finally made it to the end of this thread! So glad someone started it!
We're going back to WDW in October with our newest addition who will be 9 months (he's 6 months today.) He's exclusively BF on demand right now, but we'll be starting food soon, so I expect by the end of October he'll be nursing a little less. I BF'd with my DD in WDW when she was 2.5 months, and it was a little time consuming, but really easy. All she did at that age was nurse and sleep!
Thanks for the suggestions about rides. I have gotten more comfortable about NIP since my DS1 who is now 4. Back then I was completely awkward and nervous. My trip to Disney with my DD helped me ease up a little, but I still brought my pump and tried to give her bottles of EBM instead of feeding her. I always felt like I was inconveniencing everyone else. I never found the Baby Centers, so I sheepishly covered up with a blanket and hid in a corner, afraid of making others uncomfortable. By #3, I'm way more comfortable and probably more discrete. I am a descrete person by nature, but I've found ways to make myself feel better.

I always wear 2 tanks. Either a nursing tank (target) underneath or just a cami. I do this to cover my stomach. The top tank or tshirt covers everything else. I also just like how the first tank kinda holds in the tummy that I'm still holding onto.

I finally bought an utter cover. I actually really like it. Mine is super thin and I love that it stays on. I don't always use it, but I wish I had had it with my other two.
Some other thought related to this thread:

I love the idea of the big floppy hat. You can't tell the difference if the child is nursing or napping.

I've been a fan of the Target (Gillian O'Malley?) brand of nursing tanks, but I'll have to check out JCP, Motherhood, and a few others mentioned. I hate spending the money since this is our last baby, but I hope to be BFing to at least a year, so it's probably worth it.

Re: nursing so much while on solids... That's part of the reason I'm not starting the little one on solids exactly at 6 months. I think he's pretty much ready, but they are such a pain! Nurse, feed, nurse, feed, nurse, feed, nurse!

Re: sippy cups... both of my older ones have taken a straw at around 6-8 months. I love the Nuby fat straw cups. I practiced by dropping drops of water in their mouths with a regular straw, then got them to suck a little themselves. It didn't take long to get the idea of a straw, especially being BF.

I've exclusively nursed all 3 of my kids (DS for 11 months until he self weaned, DD until 15 months when she self weaned and because of her severe milk protein allergies.) I never thought I'd breastfeed since my mom didn't BF any of her kids. But being an RN, I knew it was best, and I wanted to just give it a try. Thankfully, my oldest didn't give me too many problems after the first 28 days of excruciating soreness. After I made it through that, it's been smooth sailing.
Here's my nod to all the women who have BF their kids for 1 day, 1 month, 1 year and beyond. It is the most beautiful, natural thing we can do as moms. You've given your babies the best start in life! Don't listen to anyone telling you otherwise!
Oh, there's so much more I thought about commenting along the way reading these 23 pages, but I'm off now before I have to get up in a few hours with the babe.