Family of 4 and we have stayed offsite, moderate and Deluxe (CR). There are a few reasons we will not stay offsite unless we are traveling with a large group (several families and friends and stay in the same house).
1. The Disney bubble is real. Can't really explain it, but there's just a different feeling when you know you are there. The staff have always gone above and beyond when needed and the cartoons in the lobby, the music in the common areas, just a little more enjoyable.
2. If desired, no driving. We usually rent a car as I like to drive and be more in control of things. However, the ability to just enjoy the buses, boats and monorail to take you where you need to go is great.
3. EMH - We will typically head to the parks in the morning, take a swim/rest break at the hottest part of the day when everything is the busiest and then head back for the evening. The morning hours mean getting your favorites done before the crowds and being able to stay out late with limited crowds in the parks is a lot of fun. At 12:30AM walking down a quiet Main Street with the lights and castle glowing. Just can't get that anywhere else.
4. Free Dining - If you are lucky enough to plan a trip when it is offered and it makes sense financially (not planning to debate if it's worth it or not), being able to just grab what you want and not worry about the bill is pretty cool. Everyone has their own band and the ability to just grab a snack or have a meal without needing to bother me. Of course my kids are older and very responsible eaters (if you don't count the occasional Funnel Cake, Mickey Bar and Waffles
) so they can just get what they need.
We have always utilized the refrigerator to have healthy snacks, milk for cereal/breakfast and whatever else we needed to keep fresh. The moderate rooms are not huge, but provide enough room for us. Our stay at CR was very nice, the monorail going through the lobby is a nice touch, but for us and our $$ we will stay moderate. Every few years when we feel like splurging, we will stay on the monorail. Poly is up next based on the consensus.
If you have the $$, it is worth it to stay on property in our opinion. If you need to take a trip and be very budget conscious, off site is your best bet. Not only can you eat and cook there, you have more access to the off site restaurants that are certainly less expensive than eating on property.