Definitely rent points to stay on property. Budget $500 for this: if you can find someone willing to rent for $10 a point (some of us still do), then you can stay 5 nights at Old Key West. If the owner asks more than $10 per point, then you can rent enough for 4 nights. Either way, you will not spend more than $500, and there is no tax. Also, no housekeeping, just a trash and towel service, so no tip needed. For the price of a value room, you will have a deluxe resort room, with a kitchenette. With the larger fridge, microwave, toaster, and coffee maker in the room, breakfast in the room will be super easy. Stock up on bottled water/soda for the park, and easy-to-carry snacks. Having a cold drink and a snack in your back-pack saves as much time as it does money...who wants to wait in line for a pretzel? I always include my weekly grocery money in my Disney budget because I am not going to be home to eat...use that money to purchase snacks and breakfast food. A family of four can easily eat for four or five days for $300, even if 1 of them is bottomless. You didn't mention any dining habits, but when my kids were younger and we were on a budget trip, I would make a reservation for a character breakfast or a nice lunch or dinner near the end of our trip. My plan was to cancel the reservation if we went over-budget during the week with our quick-service meals, but I never had to cancel. This was long before they had the Earl of Sandwich at Downtown Disney...home of the best $6 sandwich you will ever taste. I also carry in my own drink at Earl's (my kids and son-in-law like Cheerwine and Dr. Pepper) and just get a few cups of free ice. My daughter, myself, and son-in-law order 3 sandwiches and share 1 salad, for @ $20 if we use our
AAA card. We also order pizza for dinner once during each trip, so figure $20 for that. Right there you have 2 dinners for $40. I have taken teens to Disney for the last 12 years, and most will spend $10 for a meal at a quick-service restaurant without any planning. If you do the ordering for your son, though, you can order the combo for him, a combo for your Fiance, and just order an entree for yourself, as you can share their drink and fries. I usually just order a kids meal for myself, because Disney has made them a lot healthier than they used to be. I would budget $25 for each quick-service meal if I were you, especially if you were carrying a few snacks with you to help with the low blood sugar issue. And definitely carry something for the 2-year-old to eat. You can easily take a trip in September with $1000...I say go for it!