After thinking about this way more, I've decided I'm just going to conserve my 100,000 UR points from the CSR bonus and try to plan a Disney trip for next year. That way I can have time to apply for the 2 Chase SW cards at the end of the year and try to get the CP for 2017-2018 to maximize my savings. By that point I should have lots more UR points built up and should be able to plan a much bigger trip for much less. Does anyone know if you book a Disney resort hotel through the UR portal if you still qualify for the dining plan? I didn't know if you had to do a package through Disney for that or not. I know we can always just use Disney gc for our food and pay as we go, like we did on our trip next year. In fact, that's probably what we'll end up doing simply because of the cost savings involved. I was just wondering if the dining plan was even an option when booking this way.
I'm sure if I can plan this right I should be able to get a great deal on our hotel and flights. Then my husband will definitely see the savings potential here and be more on-board with what I'm doing.