Everyone - Thanks for the quick, and detailed, responses. It is why I like this site and have visited it for 10 years.
"She Who Must Be Obeyed" has added an extra day to the trip. So I figure splitting it up with one day at each park (with a parkhopper option). As a result, we may be able to see the Aladdin show, which I have heard is great (my wife and I love the Beauty and the Beast show at DHS).
Again, thank you for the prompt responses. Keep 'em coming!
I wouldn't bother with park-hopping over two days. Mid-July is one of the busiest times of the year, you may want to take the time switching between two parks to explore more.
Even if it's packed, fear not, it's really no less fun at DL because of the diversity of rides over such a short distance. That being said, it feels noticeably more like a sardine can in the walkways of DL, especially in New Orleans Square and Adventureland.
Never spend
any time without a fastpass. I would start in the morning with Space Mountain or Indiana Jones. Remember that it's a two hour window (listed at the bottom of the ticket) if the return time on your previous ticket is several hours away--you don't need to wait that long! May sound like an old tune, but it's surprising how many people forget this.
My personal advice is never to get a fastpass when the line is under 30 minutes. I know there are some advanced, very mechanical strategies that advise you to get a fastpass for something in the wee morning hours even when the line is short so you have the upper hand in experiencing other rides, but I think it's much less stressful to take chances as they come by. You can always get a FP and ride again if there's an attraction you really like.
Big Thunder is better in Florida IMO. EDIT: it'll be closed anyway, so never mind!
Try to be in Fantasyland to watch the fireworks so that you're right there when the rope drops and you can walk right on to Peter Pan, followed immediately by Mr. Toad and Alice in Wonderland. Snow White and Pinocchio are noticeably less popular. Fantasyland as a whole may be less busy during the last hour of operation, I'd save the Matterhorn for those precious final minutes before the park closes. You can skip Winnie the Pooh, Star Tours, and (dare I say it) Haunted Mansion if their waits are long, they're more or less the same as their Florida counterparts, unlike really anything else. The Subs have a special nostalgic appeal because they're freaking submarines, but the ride is very similar to WDW's, just longer. Lots of people like it though, and it's slow loading without fastpass, so if you want to ride it, it must be within the first hour after park opening.
In the crowded mid-afternoon, use the time in your fastpass windows to take a round trip on the nearest railroad (when you pass go collect $200), perhaps see Mr. Lincoln, check out Tom Sawyer Island (rethemed to pirates there), or ride Winnie the Pooh which curiously seldom has a long wait. My personal favorite areas of DL park to meander around in are Big Tunder Trail (walkway between Fantasyland and Frontierland) and New Orleans Square. Your son will enjoy Toontown, there's lots of very clever gags and streetmosphere gadgets to toy around with.
Lastly, take any advice in stride, but don't forget to experiment a little and do it your own way! It doesn't need to be highly regimented, every family has their preferences. Just be warned that crowds will be high-ish, and that it's no reason to have any less of a good time so long as you're aware beforehand. Enjoy!
