This is my Disney/Orlando profile: 1) I have stayed in most value and moderate disney resorts 2) I also have a timeshare. These are my thoughts...
As someone who absolutely loves the 24/7 disney magic - it is not a necessity when it comes to price (I travel to disney on a budget). For me, the biggest advantage to staying on Disney is the EMHs (especially morning at HS). However, that is not enough for me to spend the extra hundreds for a disney resort over my timeshare. And here is why:
1. In my timeshare which is about a 20 minute drive - I have ample space. I can get a 3 bedroom, 2 bath with whirlpool in room for 7 nights/8 days for about $500. That includes resort amenaties, parking, etc. A 7 night stay at Disney in a 3 bedroom (or 2 bedroom) according to the disney site is no less than $350/night. There is no comparison to staying in a timeshare vs disney in terms of space.
2. Magic... For me, I enjoy being able to submerse myself in disney magic for the hours I am on property. However, it is a joy for me to be able to get in my car and leave disney and go to a delicious resturant in Orlando or Kissimmee at much cheaper prices. I understand that beauty of paying $10 for a cheeseburger with a handful of fries and calling that magic but I can go to Chilis and get more food for the price. When I get back to my timeshare I can relax in my whirlpool or take a dip in the pools and be relaxed enough to wake up the next morning and do it all over again.
3. Mid day breaks: It is true that when you stay on property you can take a mid day break and utilize disney transportation and be back at your resort for a pool and lunch break. Ok - lets talk disney transportation. Depending on where you stay, what part, and how many stops the bus makes, as well as time of day - you could be waiting for a bus and sitting on the bus for extended periods of time. I have been able to arrive at the parks early enough for me to leave around 1 and drive my car back to my timeshare and return by 4 with no problems. And after a long day in the parks it is so much better for me to get in my car and be on my way.
Please note: These are my thoughts on the timeshare vs disney. I will say - if you are someone who will miss disney magic 24/7 - then you must stay on their property. I last stayed on disney property in January 2012 and for me a lot of the disney magic had decreased. And it is nothing like having your own car (on proprty or not). The only benefit to staying on proprty is EMHs and even that can be questionable depending on your travel group.
Happy travels