... to get than cheap flights. (There are some markets that are exceptions of course, but I don't live in one.) If you need to get from airport A to airport B without a lot of time wasted in layovers, your choices are relatively limited.
It does make sense to pay more attention to hotel prices with a large party/long trip than with a small/short one, and it also makes the most sense to do that if you are travelling at a busy time. Of course, that breaks the other cardinal rule of cheap travel: never go at a busy time!
I've always found it much easier to work the discounts on hotels than on flights, not least because hotel ressies can more easily be changed without losing a lot of money. There are what-- ~60,000 hotel rooms in the Disney area? Even if you are adamant about staying onsite, you have over 25,000 rooms at 22 locations to choose from and finesse into the
budget. I will check on the schedule of major events before I book a flight though; don't want to roll into the middle of the Democratic Nat'l Convention looking for a cheap room, like someone I know did. (Obviously, a very apolitical someone!)
I've also found it easier to use point programs for hotels than for flights; the airlines are a real PITA about points. This year's 5-day stay at Swan for us will cost nothing; over two years, we accumulated enough Starwood points to get the room on redemption, and there are no blackouts for that at S/D. Last stay we were @ WL for $129/nt, the time before that, POFQ for $85/nt, and the time before that, BWV on purchased points. I can just about always find hotel deals I can live with, one way or another. In my market, anyway, good prices on flights are much harder to score.