Great stories, everyone. But boy, after reading through some of these posts, I feel like a fool. Here's how I ended up proposing (I say ended up, since it really didn't go as planned!).
June 1999 - So, I buy the ring, we plan the trip and it's time to go. We had decided to drive and take her car, which made hiding the ring a task, especially since we still lived with our respective parents at the time. So, me being a car guy, decides that I'll give the car a once over to make sure it's good for the trip, and wash and wax it (gotta make it long, so that she'll take my car and go home...hehehe). For some reason (which I don't remember), I didn't want to hide the ring in my suitcase. So during the time I had the car, I slipped the ring (in the box, of course) under the spare tire in the trunk. Later, she came and picked up the car and went home. He he, she had no idea. I like it that way.
Fast forward to WDW. We hit MK first (of course!) and when we parked, I managed to slip the ring box into my....ahem-fannypack-ahem. We go from start to finish, and end up in Liberty Square to watch the Electric Light Parade that starts shortly. Here's where the "magic" is going to happen. No pun intended.
"OK Dave, gather yourself, you've been with her for a long time, so this should be easy." Yeah right.
As she's looking on, I manage to slip into my pack, get the box out, and slip it into the leg of my baggy shorts, under my thigh. "Whoa, she almost saw that. OK, deep breath, here we go." As I slip my hand under my leg to get the box, a train of kids and adults come walking by and now there's no place for me to kneel down. As their train ended, another one was coming from the other direction. "You gotta be kidding me!", I say to myself.
As I finally have a clear path, out go the lights. Good thing the ring box has a little light built in that shines down on the rock. "This ring is going to look awesome in the dark with the light on it." For some reason, my nerves just don't allow me to do the deed. I'm beating myself up.
"Would you just do it? Uh-oh...oh no! Here comes the parade! I waited too long! OK, OK, don't sweat it, just do it after." (I'll find out that waiting until the end wasn't a good idea!)
We watch the final part of the ELP, everyone is clapping and cheering loudly. I look at her, grab the box, inhale and....WHAM! People everywhere! If I thought there was no room when the families walked by before the parade, there SURELY wasn't any room now.

"#*%!@#*^%$#!!!!" Over the PA, they are asking that everyone head toward the exit. "Come on, let's get outta here", she says. "Not yet, let's wait until the crowd gets ahead of us." It went on like this for a few minutes until she got real insistent, and a CM was walking by and instructing everyone to head to the exit. "Dang", I thought. I was pretty upset by this point, not believing that I had chickened out to this point.
The crowd had made some good distance on us, that by the time we reached Cindy's castle, it was pretty empty. "Perfect! This is it!! Oh...who's that over there looking over here? Hmm, lemme stall. Hey Hon! Come stand over here so I can take a picture of you in front of the castle!" I stalled through 4 or 5 pictures, and STILL couldn't do it. I don't know what I was so nervous about. Over the PA, a message stating the last tram time came on, and we realized that time was quickly approaching, so off we went. I felt defeated.
We get to Grumpy's parking section and hopped off the tram. As we get to the car, I decide that this is it.
For real. Really. No kidding this time.
I open the door for her, she gets in, and I kneel. She then looks at me wierd and says, "What the heck are you doing?"
And the rest, as they say, is history.
