The $282 is a really good rate, especially for a view room. I just took a look at the AP availability calendar and it's kind of strange that the view room is LESS expensive than the standard! Who would have guessed?

Especially since it's less over the weekend and then pops back up in price for a Sunday night. As for being upgraded, DH and I have stayed at the DLH twice and at the GCH once. We were upgraded to a pool view and a DTD view on our two stays at the DLH. We booked a standard room and got a standard room (nice view of the roof with a tiny peek of the pool if you stood and tilted your head just right) when we booked at the GCH.
I've heard it mentioned a few times from people who have received unasked for upgrades that a) they went during slow times (and the availability at all three resort hotels in all but one category at DLH indicates this is probably a slow time) and b) they booked well in advance. Both of those factors would make sense with the two times we received an upgrade. The DLH trips were booked about 3-4 months in advance at relatively slower, mid-week times and the GCH trip was booked about six weeks in advance over a busy weekend.
If I were in your same position, I would probably go for the one extra day in a standard room knowing that chances are I would need to be moved (but hold a tiny little flicker of hope they might keep us in the view room for our entire trip). I would probably ask on Saturday afternoon or Sunday morning if they would consider letting you keep your existing room. After all, it would be less cleaning for them then having to move you to a completely new room for one night.
For our Labor Day weekend trip where all three hotels are completely booked on the Friday and Saturday nights of our stay,

I'm just hoping we don't end up in a converted closet.