Here are a few suggestions
I don’t suggest booking through Disney. There are no discounts and you have to pay in advance. I book directly with the hotels (unless staying on-site). Purchase your tickets separately. Again, when they are packaged together you don’t get any breaks and you pay in advance.
If you want to stay off-site and want to be really close, my favorite is the Best Western Park Place Inn. It is the closest off-site hotel. It is right out of the park gates. When my 9 year old was younger, we would stay there and go back for naps in the afternoon. It worked out great. My next favorite is a couple of doors down at the Marriott Fairfield Inn. A really short walk.
For character dining, it depends on who you want to see. Do you have a preference? We have done them all.
When we fly in and start with DLR, we usually will take a shuttle to the resort and then pick-up our rental car from Alamo in Downtown Disney. That way we are not paying to park a car we are not using at the hotel.