Originally posted by jordanyosh
You are probably asking the wrong group of folks....
I would strongly recommend that you heed the above words. Most of the comments I've read in response to your question have been overwhelmingly in favor of spending the extra money to stay on property. Keep in mind, this is coming from the same people who generally believe Disney can do no wrong, so you have to factor in a certain level of bias.
Having stated that, here is MY input (for what it's worth)...
Staying on-property is definitely preferable, no doubt about it. I've stayed at about half the hotels on property, from All Star Resorts to the Yacht and Beach Club, and every one of them is better than anything offsite (I've also stayed at quite a few offsite hotels). If you're familiar with my previous posts, you know that I love Disney with a passion, but that I'm quick to criticize things I don't like, and I never pull punches. Hopefully that lends some credibility to my claim that Disney resorts are superior. The service is outstanding. The rooms are generally immaculately clean. And there is a certain "magic" that makes it even more special. And let's face it, isn't escapism one of the primary reasons for visiting WDW in the first place? When you stay on property, you extend that experience of being in another world.
However, there are still some additional things to consider. 30% more can be hefty and you might want to consider some other things that you could apply those extra dollars to. For example, you could probably rent a car for the week for that extra expense. Despite what everyone says, I have never considered the bus transportation to be an argument in favor of staying on property. I personally DON'T find it all that convenient, and you're restricted to the bus schedule (whereas, with a rental car you can come and go as you please and on YOUR schedule). We ALWAYS rent a car, whether or not we're staying on property. You could also apply those extra dollars to a special event, a dinner show, extra souvenirs, etc. Is it really worth paying an extra 30% just to have Mickey call you and wake you up in the morning?
Bottom line, on property is definitely better, without question. Whether it's worth the extra money depends on your priorities.
Don't know if that has helped much, but that's my input.