Hi Christina,
You have already made the big decision to go to WDW and have committed to dates. You are really more than half way through your planning. Try not to get overwhelmed. The first thing to remember is that you can't experience everything at WDW during one trip. Think of WDW as a city that you are visiting and try to see as much as you can comfortably.
The Magic Your Way package is a way of buying your park tickets and WDW resort stay all in one transaction. It is very convenient because your park tickets are loaded on your room key. Your room key can also have charging privileges so that you don't have to carry cash or credit cards with you. Take some time to review the
vacation package website.
You don't need to make dinning reservation. Don't worry you will always be able to find a meal at WDW. Each park and resort has counter service restaurants that offer a variety of foods. However, many of the table service restaurants are very popular and do require reservation. WDW is very large and attracts 10s of thousands of people a day. The vast majority of them what to eat at a table service restaurant. It would be much too chaotic without a reservation system. It is much easier to get a reservation or obtain a walk-in seat if you try to eat during off hours like having dinner at 4:30 or 8:30pm instead of 6pm.
I'm sure your son will love being in WDW for his birthday. You may let him pick what attractions the family does on his special day. You can also treat him to a unique experience like a trip to the Pirates League or Ridemakerz. You can also try to get a reservation for a character buffet on his birthday. Check out the online reservation system for availability.
Please stop back and ask us any other questions that might come up.