Hi Christian,
I'm so excited that you are planning your first trip to Disney for your 5 children! I have oodles of tips that I can give you, so I'll stick with your specific questions and you can send me any follow-ups that you may have.
I recommend the
Plus Dining package. This includes one Table Service, one Quick Service and one snack per person, per day. We have found with our kids that we
need the one sit down meal a day to re-group, rest and relax for a bit. However, any more than that and it becomes work. The kids want to be in the parks, enjoying the rides. To make the most of your time, book some character dining meals. This will save you from having to stand in long lines to see the characters while in the park. Chef Mickey's and Crystal Place are great. If you have any little girls, you'll want to see the Princesses too. Call 407-WDW-DINE to book your dining reservations now. These fill up quickly.
For your littlest 2, I recommend that you bring a double stroller from home. While the park strollers are sturdy, they aren't known for being comfortable. Having your own will make it easier for them to nap on the go.
I also suggest that you purchase the Base tickets and stick to one park per day. This way, you can fully immerse yourself in the magic. The amount of work involved in moving 5 kids from one park to the next is a lot. You may as well just get there in the morning and make a day of it.
Please let me know what other questions you have.
Have a wonderful vacation,
Kaylene