I am planning a trip for November 2020 and was wondering if it is worth the extra money to stay at a Deluxe resort over a Moderate. My kids will be 2 and 4 so I was thinking Wilderness Lodge because it has a boat to Magic Kingdom and that is probably where we will want to go the most. However, I could save over $2,000 staying at a Moderate resort during the same time frame. Is it worth all that money to stay at a higher tier hotel? I know it would definitely be more convenient, but I am having trouble wrapping my mind around the price.
This is such a tough question and personal. So I will answer it with my personal experience. I also have two kids but mine are now 11 and 12. When our girls were younger and we spent less long days at the parks and more time at the resort, I felt like Value/Mod was the way to go since-
A- my kids don't really need space
B- they didn't care if we stayed at a dump or a nice hotel, staying in a hotel was a novelty enough to them so it was always fun.
C- theming at the values was better suited IMO for young children.
D- all they cared about was the pool
The transportation is a big convenience factor with strollers and little kids in tow so you do pay a hefty price tag for that. We didn't mind the bus but we've also thrown in the minnie van on our last bunch of trips and it's awesome. Even though I don't have strollers anymore, you cannot beat the convenience so even if you took a Minnie Van every day of your trip, likely multiple times per day, it wouldn't be at $2K so you could stay further off property and do that over paying for WL.
I think it comes down to priorities. You just need to list your pros and cons and see how it all shakes out. If transport was my #1 driving factor in my stay, I'd look at a Monorail resort as opposed to WL. The boat is nice but the monorail is more convenient and of course, walking from the Contemporary can't be beat.
For us now with older kids, we do mods/deluxe for the 5th sleeper option and we pay more for that, but I wouldn't want to be on the hook for $2K more. Even the crazy Disney fan that I am, I draw the line on what's worth extra for us.