I recently took a trip to WDW with my redneck newbie relatives and had to listen to an intense conversation comparing and contrasting the skills of Dale Earnhardt Jr. and Jeff Gordon [NASCAR] that consisted of win/loss records, pit crews, sponsorships, etc.
Here are some thoughts...
1. Everything is too expensive. We planned an evening at WCC (which they liked), but...it was too expensive. Breakfast at Chef Mickey's with the kids...too expensive. Pecos Bills - too expensive - or actually poor value for the money.
I had suggested the dining plan, but was told it was too expensive. I wish I would have insisted on the dining plan.
2. Access to off property. This is related to #1. Since everything was so expensive, everyone insisted on being able to get off Disney property to go look for food. (They commented later that they felt trapped.) Since you are probably flying...rent a car and stay at a resort that has easy access to the car.
3. Hotel Rooms - Since this was our 1st trip using DVC, DH insisted that we stay at our home resort (Boardwalk). Too Swanky. They felt uncomfortable, and had trouble getting back to the truck to go off property. (Being a little bit of a redneck myself, I have to admit that I feel more comfortable with the people at the value and moderate resorts.) POR is absolutely perfect!!!
4. Smoking - Relatives pointed out that the smoking areas were few and far between, and not posted very well. This was before the no smoking policy at the resorts. Request a room near the smoking areas.
5. Focusing on Country - Be very careful here. Everything Disney does is a fantasy or "play-on" the real thing. Sometimes with the country stuff...it comes off as pandering. The family loved Whispering Canyon, but commented that the bumpy road on the safari was over the top. Why imitate a bumpy road? At home we are still trying to get rid of bumpy gravel roads. Frontierland is one of our favorites. DH and I kind of felt pandered to at Hoop-Dee-Doo Review, but in Alabama a lot of the tourist stuff is centered around stuff that looks a lot like Hoop Dee Doo. I was far more impressed with the Luau. (I have no idea what an authentic luau is supposed to be like, but I grew up around plays featuring red necks.)
I wouldn't automatically send this guy to Ft. Wilderness. If he is at WDW, he will want to see WDW. Fishing is nice, but remember its catch and release. How much fun is that? Why play fish when he can go home and do the real thing?
Let him know that WDW is a big place with lots to do, and that you encourage him to find out what is available, and to plan ahead.
By the way...the folks were blown away by Wishes and Illuminations, but was overall overwhelmed by the experience.