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raven24 I know you helped me a ton when we planned our DL trip last year. Hopefully you can get the same amount of help from all of us DW vets!
I really think you should stay on site if you can. The 'bubble' is very different at DW than at DL. Plus the extra magic hours are a great benefit for on site guests. It is similar to DL, except that it can be evening hours and sometimes the parks stay open till 2am for on site guests only. It can be a lot of fun walking around the parks at that time in the morning!
Between All Stars and Pop - I preferred All Stars. All Star Movies was my favorite. I liked the food court better (well... besides missing the tie dye cheesecake from Pop) and I had better experiences with the buses at Movies as well. But really, either choice is a great one!
I don't know what your dining plans are.... but one thing that is very different at DW vs DL is dining. I loved how at DL you could walk into a table service restaurant and just be seated. No reservation required. You can definitely get into some table service restaurants without reservations at DW, but it is going to be much harder to do. If you plan on doing TS, you will probably want to make reservations and if you stay onsite you can do that 180 days in advance. (and at 180 days - you can make reservations for the next 10 days of your trip... so 180+10 that we often talk about here!)
Have fun planning and ask lots of questions!