[FIrst of all, relax. The DIS is home to many uber-planners. They simply can't imagine going to WDw without LOTS of planning. IT doesn't mean that's the only path toa great WDw visit (despite the doom and gloom posts) While I typically do some minimal planning - I've also done many great last minute trips. Shh, usually the spontanious ones are the most fun.
At a good number of places, you may be able to get a table walk up, especially if you show up just when they are opening. However, if you try that at the truly high demand places: Le Cellier, 'Ohana, Cali Grill, CP - you are just wasting your time - and often a considerable amount of time at that if you are traveling via bus. Those four especially come to mind in that they are not firendly when they are turning guests away. Cali greeters aren't even warm to those with ADR's!
You should most certainly check back. I wouldn't bother checking every day because there aren't likely to be many cancelations two weeks in advance - BUT - the day before or the day you want to go there are likely to be cancelations- especially if there is a big storm running across the country (canceling flights). It wouldn't hurt to chekc ina few times inthe next two weeks, but most folks don't cancel two weeks out. (all packages are paid at the 45 day mark). You've also got better odds on a day with lousy weather. Folks may not feel like going across property in heavy rain just for dinner.
I would also encourage you to consider some other places. If it's steak you want, there's excellent steak to be had a short distance from Le Cellier: either Shula's or the YC steakhouse.
In place of Cali, try Narcoosee's (in GF) or Flying Fish. Personally, our family greatly prefers the food, atmosphere, service, and view at Narcoosee's over Cali - and ADR's are easier to get there. Flying Fish also has very good food, if not the same kind of view.
If none of that works....there's one other suggestion that might: feed you son ahead of your 9pm ADR. If you think he'll fall asleep, then it won't work. If you think he'll be awake, but just want to eat before then - then you could most certainly grab quick serve dinner for him. It may be fun also for everyone to have aquick serve dinner and head to a place like Cali at 9pm to have just dessert. That can also be done.
As for quick serve places, they've come a long way. Indeed, several of them even serve the same food. The Mara serves Boma's signature soups and desserts. Pretty sure WL's quick serve also has a few selections from WCC. The quick serve places inthe World Showcase also have some high quality food. Morocco has really great food, the QS bakeries in France and Norway have some of the best desserts on property! Also, if you don't have
DDP, consider the excellent offerings at the Swan/Dolphin. Some of the dining there and at the BWK do not do reservations, but are very good offerings. The ones that do take ADR's don't often get full, simply because they aren't part of DDP and Disney's free parking.
