-Not going to do a character meal, waste of money. Of course I told him, he has to do at least 1!! (and most of you guys know I hate buffets)
IMHO, a lot of people end up really stressing themselves out at Disney because they go in with a whole list of "Have Tos." My middle daughter was stressing out at first because her friends said she "had to" do this or that ride that didn't appeal to her at all -- I finally sat her down and told her the only things she "had to" do were things that she desperately wanted to do, and that she was only allowed a maximum of five "have tos" anyhow. Memory serves, her "have to dos" were the Pirates of Caribbean Ride, the Pirate Tutorial, Tom Sawyer Island, the Move It! Shake It! parade, and the monorail,
none of which were on the "have to" lists her friends offered.
This guy clearly doesn't want to make rope drop, and he doesn't want to stress out about having to herd three kids around, so I'd recommend you encourage him to go in with the idea that they are NOT going to "do everything" or go for the "classic WDW experience" or whatever. People who don't like to do rope drop and don't like to rush can still have a good time, so long as they don't expect to get on many - or any - of the really popular rides. I'd tell him stuff like, "If there's a huge line for Dumbo, go for the Magic Carpet Ride instead." "Here's a list of rides that are easy to get on most of the time."
I'd also offer him the schedule for stuff like the Pirate Tutorial or the glass blowing or the Frontier Hoedown at the MK; Kim Possible and the Jammitors at Epcot; TamTams and GiTarDan at Animal Kingdom; Mulch, Sweat and Tears or the Characters in the Animation Courtyard or wherever at the Studios. Stuff that most people aren't looking for that doesn't cost extra and is kind of random, thus easier to access. A lot of people who "hate" WDW actually hate the crowds, the lines, the hustle and bustle, and/or the rides, so offer him another view of things.
Could be, he goes in with a "go with the flow" attitude, knowing how to find things his kids would enjoy that don't have a huge line and aren't a big hassle, he might find he actually likes the place. If not, maybe you could help him destress enough to enjoy his kids' enjoyment.