We recently returned from a stay at CBR with a 5yo on a first trip. We found the resort to be lovely, convenient with plenty to keep him busy. We also loved the transportation system and used it all buses, boats and the monorail. It was my first time on site and wouldn't choose to Disney any other way. The
DDP really made it feel like a vacation and the food court at CBR was clean, convenient and had a really nice variety. My biggest plug for staying on property (SOG is not) is access to the EMH. Knowing you can get an extra hour in the morning (we only did the Little Ones Magic Hour) or 3hrs at night allows you to take a more leisurely pace during the day. I will give you an example of our Day 3 (Sun Sep 2nd)
Wake late and head over to food court for breakfast at around 10am
Eat the head out to the pool directly from the food court
Pool time and walk over to Caribbean Cay (think that's right)
Out of pool around noon to clean up and head to Animal Kingdom
Arrive at AK about 1:30 or so, grab a stroller (first time on the trip)
Head to 2pm Lion King show (stopping in Oasis to check out animals)
Enjoy the show and grab ice cream from a cart on the way to next stop Character greeting with Flipper? (Bug from Bug's Life), fun photos
Rode Wildernss Express train to Rafiki's Planet watch, enjoyed activities there
Character greetings with Rafiki and Pocohantas, nature talks/exhibits
AK Parade was passing by when we exited train, caught the end
Headed toward Nemo, stopped at a fantastic spot to catch the entire parade
Arrived at Nemo in time for final show, walked right in
Exit park and took bus to AK Lodge for dinner at Boma, took in savannah view and time at playground while awaiting our table (took pager with us)
Dinner at Boma was great, food and company at neighboring tables
Took bus to Epcot and caught Illuminations, took monorails to MK for EMH
Little one selected his ears at the Chapeau near the entrance at MK
Watched the full Wishes show (night before little one was scared of fireworks)
Fantastic character greetings in Fantasyland (Pluto, Goofy, Chip and Dale)
Mickey and Minnie were also there, but we opted to skip those lines
Some ride lines were long (50mins for Peter Pan, but 10 for Small World)
Closed down MK with sleeping 5yo in stroller, he lasted 'til just past midnight
Had we been concerned with getting it all in we would not have taken the entire morning "off" at the resort. The EMH gave us that option. My nephew loved the pool time and we loved the rest too.
Breakfast, ice cream and Boma were all on the DDP
EHM and Disney transportation gave us a lot of flexibility, with Magical Express and Disney transportation I would never rent a car for a Disney trip
I can't be as familiar with SOG as you will be, but if the money is so similar and the benefits a bit better at CBR I can recommend that choice. To still be able to treat yourself to a cruise later is icing on the cake!
Sorry to be long winded, but sometimes a picture is worth a thousand words.
If this is a 2008 trip please check the pool rehab schedule for CBR to decide if that will be OK for you.