He is more of sit on the beach with a drink and not move kind of vacationer. I don't think he is looking forward to crowds or lines. I know this about him which is why I'm planning to go at a time of low crowds and plan for some resort days
My DH was like that too! That trip to AKL in 2003 in my signature? It was a long weekend in early December and I was up early to walk around the resort, watch the animals and then catch the bus for EMH
; he was like, "I'm on vacation! Let me sleep in ...." I remember we'd take vacations to the Caribbean or beach resorts, and he'd want to spend the whole day lying out on the beach, and I'd go in the water, read a book, sit for a while, and be like, "ok, now what?" and it was 11am.... lol.
My husband said the same thing when we went for the first time when my kids were 4 and 2.5. We are going again for our fourth time since then this summer when they will be 7 and 5! He is hooked now too!
Fast forward to we finally have kids, I've been going since I was a kid, my younger sister since she was 1. WDW is my happy place, partly because it has so many great associations to my own childhood. DH never went with his parents, and went once in HS with his band before I started dragging him in 1993. My mom organized a family reunion offsite in 2013 when ODD was under 2, and she loved it, though she doesn't really remember it and we could have been anywhere. So DH, ODD and I stayed onsite in August 2014 just before she turned 3, was "Saved" a ton on tickets, food, etc. because she was free, and she still loved it. One night she had a meltdown with DH while I was riding space mountain, and he yelled, "WE ARE NOT COMING BACK HERE FOR A LONG TIME!!!!" He slept in the next morning, I took DD to Epcot, we had a blast, and we were back 8 months later... LOL. I think 2.5-almost 3 is a hard time, (DH: "There's a reason why they're free under 3!") and now he's loving it. from our 2015 trip (ODD was 3.5) she's really remembered a LOT, and the magic has not worn off at all. It will be interesting, YDD will be about 21 months when we go, so the same age ODD was on her first trip, so she'll probably have fun. It's fun for us and for the kids at all ages; there's stuff to do differently, etc. One thing we hadn't realized until we stayed on site and went more often, is how much stuff there is for adults and how you can have very different vacation experiences. If he is a not-move-much sort of vacationer I'd suggest at least a few days, if you can swing it, at a deluxe where he can hang out at the pools, on the resort grounds, etc and be at his own pace, and you can take the kids to a park if they want. The most magical times with my kids started at 3.5 - I look back at some of the pictures and the looks on their faces.... they're so enthralled.
ETA: My ODD remembers *a lot* starting with the BWV 2015 trip, when she was 3.5. They may blur together, but she definitely remembers.