Does it get old? No. I went many times as a child and my DW didn't so for her she's still experiencing a lot of things for the first time (so am I.) For example, neither of us had ever ridden Space Mountain nor Big Thunder Mountain and so since we've been married we got to experience those things together for the first time (space Mountain for the only time lol.) For us, it's all about experiences. You never know when you're going to see a CM interact with someone in a special way (or with you for that matter.) Granted there are those not so magical experiences from time to time but you have to overlook them in favor of the good ones. We attended
MNSSHP for the first time last year and it totally renewed our love for WDW. The Mad Hatter, Alice, Tweedle Dee & Dum both got out of the Boo To You parade and danced with us on Main Street because we were bopping along to the music (it's very catchy if you've never heard it.) I'm 32 now and have been to WDW at least 30 times and that will go down as my best trip yet so as you can see, there's always a new magical experience just waiting around the corner.
How does Disney feel to you, versus the first few visits? Still magical. As someone else said, walking in and seeing the castle at the end of Main Street never gets old. The sights and sounds of main street, especially right after rope drop, just bring back so many memories. Again, having gone as a child, I still usually cry during the fireworks or the electrical parade just because I think back to the times I stood there with my mom & dad watching them. It's a very nostalgic experience for me.
How is your touring style different? What
IS your touring style now? We don't sweat it. We know if we miss something this time, we'll be back again. Also, we never used to do FastPass at all but I'm one of those now that feels like I have to (I know you don't.) We typically will navigate the same path through the parks every time so I'll book our FastPass+'s around the time I think we'll be in that area. Sometimes we need to use them, sometimes we don't. I never fool with getting the rolling extra FastPass, just not worth the trouble for me.
What’s important to you on your stays, since that you’ve pretty much experienced it all? The classic rides, HM, POTC, Jungle Cruise (or Jingle Cruise if it's during the holidays.) For us, 2 adults and no kids it's all about spending time together and there's no place we'd rather spend it than WDW.