For our upcoming trip we were also considering off site vs. on site. The off site price was awesome.. But we felt the on site perks outweighed the off site price. We are the type of people that like the whole "disney experience.". We love being immersed in it, from the room, to the parks, to the buses! So that's something you should decide of its important to you or not. Another big reason we chose on site was the transportation. We are flying in, so we didn't want to deal with rental cars, parking or a car seat situation for our daughter. Plus, you can't beat the Magical Express, which not only transports you to your resort from the airport, but it also takes care of your luggage by transporting it and delivering it to your room. Also, if you dont stay on site, I don't think you can take advantage of the magic bands. Those were something we definitely wanted to be a part of. And, if the Dining Plan is something you are interested in, you need to stay on Disney property. The off site hotels are gorgeous, and the prices are amazing... But they have to be in order to compete with Disney. I suppose the first step is deciding which aspects of your trip are important to you... What kind of experience do you want to have? Each has their perks, you just need to figure out which perks better suit your family and situation.