We're traveling with my parents for their first Disney trip in almost 25 years (leaving in 2 weeks!!). I'm so excited for this trip and I am definitely "in charge" because they have no idea what they're doing, but not knowing how they'll react to the environment, my planning has been very loose for this trip. The last time I went to WDW with them, we stayed in Kissimmee because there were only 3 resorts and they were booking at 18 months out. HS was only a year old and AK probably didn't even exist on paper yet! Oh and they were highly energetic 35-year-olds and neither had any health problems yet.
It's been easy for us to transition to vacationing together as adults. My parents treated me with the same respect that they would treat another adult from the time I was in my early teens. They've always allowed me to be as independent as I wanted to be and I've stayed very close to them as a result. Dad and I sometimes get under each other's skin, but that's just because we're a lot alike. My dad is a different person when he's on vacation, so I'm looking forward to spending some quality time with him. I have some close friends my age, but I'm more inclined to hang out with mom than any of my other friends. DH gets along splendidly with my parents, so I expect this trip to be a lot of fun.
I expect that we'll stick together. Both of my parents are nearly 60 and they've never been big "amusement park ride people", but even with my dad's heart condition and bad knees and my mom's epilepsy, there are very few rides that we can't do together at WDW. We're only skipping the mountains, ToT, RnR, Mission Space, Dinosaur, and probably Star Tours (Benn and I might sneak a quick ride). Mom will sit out the tea cups and possibly the Dumbo-like rides and we'll be taking nap breaks because spinning and lack of rest are two things that trigger symptoms for her. Everything else is tame enough that we shouldn't have any issues. We'll spend time enjoying the street entertainment, visiting the rose garden (if the hub construction hasn't disturbed it yet) and taking in the sights, smells, and tastes of the Food & Garden Festival.