My husband and I have a very high combined income, essentially we have a money tree. We do not have any bills, our home was purchased with cash and we live in a high cost of living area.
That said, nearly every trip to Disney is spent on property at a Value resort, we go at least one time per year for a week. The Values are a clean bed. I agree with others regarding transportation (we hate the bus--there is nothing magical about standing around and waiting), but can typically rent a car at MCO for $100-150 per week. This works for us. We are serious park hoppers, and with a car I can go to AK in the morning, go play a round of putt putt golf, and then go back to the MK for the afternoon--sneaking in a nap too.
If Disney does not have any "deals" (not really a concern lately) we will stay off site, at a "better brand". As someone who travels extensively for work, I must say that Disney's idea of Deluxe, is not very Deluxe. Their Deluxe hotels are at best on par with a mid-level Marriott, but with prices for an Inter-Continental. There are much nicer hotels located near Walt Disney World.
The only way I can see our hotel usage changing, is if we have a child. At this time it is only my husband and I. If we had a young child, who was into the MK and into napping I would probably stay at the Contemporary. I know everyone likes being on the monorail, but those lines for the resorts are crazy long at the end of the night (and sometimes mid-day). If you stay at the Contemporary you can walk back from the MK and not have to wait for the monorail, something that I could see adding true value when Jr. is having a meltdown.
Sometimes I think people forget that Disney is a theme park. If you took away the 4 parks, none of their other activities would warrant a resort, nor the deluxe pricing. If you want a true resort vacation, go to a nice Fairmont or an Inter-Continental where you can get 5 star accommodations, high quality dining, and activities and pools that are unsurpassed. Since we want to go to a theme park, where we wear our shorts from Target (not our resort wear from Neiman's), we are plenty comfortable in a Value.
That's how we do it, and yes OP I think a $350 hotel night "deal" is a bit nutty. It does make me hope these are fully funding their 401K's, Roth's (if their under the income max), their kids college funds, and aren't paying for today's hotel room, by borrowing from their future's. But ultimately it's not my concern, that's why it's called personal responsibility.
(If the Value's are the wrong side of the monorail tracks, me and the Potato Head family [see giant Potato Heads in POP] are happy to be there).