Thank you for all the opinions and words of wisdom! I appreciate all of the insights from onsite and offsite Disney fans. To comment on a few things:
We have driven our family of 7 to Florida and back two times, in a minivan. So, I know we can fit everything we need. Last year we managed to fit a double bob jogging stroller, a pack n' play and all of our items, so we can do it. My husband is a packing Houdini! One thing we always do for road trips is pack our clothing and other items in plastic bins that can stack instead of suitcases and duffel bags. It saves a ton of space!
We will NOT fit into a single Lyft or Uber, even if it is a minivan because on the Uber app it specifically says that Uber XL is for up to 6 people. I imagine it would be a liability for the driver, but I don't know since I have only taken one Uber ride, and without all my kids. Maybe if we lucked out with a van that seats 8, but no guarantees on this. Also, we would need a car seat for our 2 year old. The car seat is an available Uber option in Orlando (very few cities offer this service), but it does cut down on the number of available uber drivers that would suit our needs. Not only do we need a large vehicle, we need a car seat too. It makes logistics difficult and we could be stuck for a while without an available vehicle. I think we would have to do two ubers and split up and that gets pricey.
Onsite is not an option for us. It would hands down be much more expensive- no matter how many shuttle rides we get for free. Although someday I will make it work! Staying onsite in a deluxe is on my bucket list.
After discussing this at home, we have figured out some things! If direct flights drop a bit closer to the dates (like, $99 fares each way), then we will fly AND rent a car. We are BJs members and they tend to have better deals, so we will go with them. I did price out picking up car at another location but I think this is too much hassle and not worth the savings. Being able to leave the airport in a car will be much easier with the kids. If we can keep our overall transportation cost at or under $2000 for 7 people, we are doing OK. As someone stated above, rental car prices could continue to drop so we will wait it out and see if we can get a better price than $500.
If flights do not come down to $1500 or under for all of us, then we will service our car and drive. We can manage it and the responses above about the reliability of Toyota has given me major peace of mind. I trust this community and its advice!!!
With all this said, I cancelled our reservation at Doubletree Suites. I love the idea of the Extra Magic Hours, but I can live without it (boo hoo!). We can't justify staying at this particular hotel with a car since it's $27/day to park. The nightly rate is reasonable at $162 through Hilton Honors, but a condo offsite will be anywhere from $95-$130, and that's a better price given that it will come with free parking, a washer/dryer and a full kitchen.
I have changed my mind so many times about the logistics of this trip (I always do), but talking it out on the forums always help me narrow down what we actually want and what we can afford. In the future, I would really like to rent a sweet RV and stay at the campground! They have decent RV rates, but the Disney campground nightly fee is pretty high in the summer (over $150/night), so that puts that out of reach for us this year. Maybe someday!!!