Hi Janel,
Welcome back to the Disney Parks Moms Panel! Thank you for bringing these questions to us!
Having been to the Walt Disney World Resort in both July and August, I can say that there is one common characteristic - it is hot! So just plan for the weather. We always have a blast regardless. The last time we went in August, the price was slightly cheaper and we went the week that the kids went back to school in Florida, so it was less crowded.
On our first trip with our girls to the Walt Disney World Resort, we stayed in a two-bedroom villa at
Disney's Saratoga Springs Resort & Spa. We loved the villa because it had two bathrooms, a washer/dryer and a full-sized refrigerator with freezer. Our villa was in the Springs area and was a relatively easy walk to the two main pool areas. We were in the 4000 building and it worked well for us. Our building was also close to transportation and the Turf Club Bar and Grill. I will offer one word of caution - our room was on the third floor and that was difficult after returning from a long day in the parks.
We just returned from a trip where we did not purchase a
dining plan and we missed it! I definitely suggest a dining plan because it gives a more "all-inclusive feel." I also believe that we save money on the dining plan because each meal includes a drink and table service meals also include dessert. With the dining plan, you also get resort refillable mugs. These mugs are awesome to use at the resort! Finally, with the dining plan you get snacks. We use these to get frozen treats.
Janel, overall, I think the dining plan is a good value, but you know your family best!
Magic, memories and Minnie Mouse hugs,
Donyell