Scottish.Mickey, I’ve missed you!
The Poly would be my number one pick, as well. The greatest thing about the Poly (well, IMO) is the monorail access. Staying at a monorail resort makes transportation to MK and Epcot so much easier. The resort itself is lovely, and a favorite of many MBers.
Now, if you do decide to go with the Poly, I’d recommend that you book well in advance. The biggest problem we’ve had with trying to book the Poly is that it’s a popular resort, and the standard view rooms sell out quickly, leaving expensive $550/night MK view rooms available. You didn’t mention GF, but on many occasions, it is actually much less expensive than the Poly. We have found many great last-minute deals for the GF.
We just came back from a stay at the Wilderness Lodge, and it is a wonderful resort. However, we said that we would only want to stay there in the winter because it feels like a ski lodge. Idk if that would be a factor for you. The boat transportation to MK was very nice and quick, but my first choice would have been the monorail. WLR typically has great rates - some of the best for deluxe resorts. You totally get the bang for your buck here.
Now, while I’m thinking of that… consider renting points!!! There are a few MBers who rent points out, and there are many options on the DVC Rent/Trade Board on DISboards (DVC-Rent/Trade - The DIS Discussion Forums - DISboards.com). You can find points charts for 2010 (2011 will be up soon!) at DVCNews.com - The essential Vacation Club resource! - Home. This makes many resort hotels (such as Bay Lake Tower with monorail access and the lovely Boardwalk resorts, plus Villas at WLR) much more affordable.
CBR… haven’t stayed there, so I don’t have much to say about that, but the pirate rooms look really cool. Maybe if you decide that you don’t want to spend the money for a deluxe resort, you can spend a little extra at CBR and get a pirate room.
Whatever you decide, I’m sure you’ll have a blast. Mother-Son trip is gonna be so much fun! I’m already anticipating your TR!!!