Perhaps I would be if I didn't have an issue with coming up off all that money for just a room that in some cases isn't any better than a local Hilton in my own city. I do love some of the deluxe resorts - I've been guilty walking around their properties when dining or doing other activities there wondering what it would be like to stay there. However, I have to admit it though part of my wanting to stay there isn't so much about the property itself although lovely, it's about the perceived status that comes with those resort stays. We like to go to Disney yearly or at least every other year so our mod of choice CSR suits us just fine. Space enough for me and my two kids, beautiful grounds, great main pool and several quiet pools, TS dining and fairly decent QS, and the bus service is great.
Next year both of my girls will celebrate milestones with the older one graduating from high school so a long trip to Disney is out. I'm taking her to London for two weeks. However, I am planning to take my youngest daughter to Disney for four nights since she is graduating elementary school and for the first time I will consider going deluxe. I'm thinking WL because I've visited and dined at the property several times and I really like it - not to mention I think it's one of the more affordable deluxe resorts so I should be able to swing it for a short trip. With that in mind that visit may sway me to the side of staying on deluxe properties from there out but if the price isn't right I have no problem whatsoever in returning to CSR.
Edit - Just for fun I checked to see how much it would be to upgrade to WL for our upcoming Aug trip and even with the 30% off discount it's still be an additional 125 dollars each night. At this stage in the planning process that is something me and my one income can't swing. I don't want to bite off more than I can chew simply to say we're staying deluxe. My kids really like CSR - to them the resort is great and it has nothing to do with status or price points they just like it. 9 nights at CSR with plenty of money in our budget is just right for us for now.