Just to clarify this availability, we are talking October and November here for
@jenmsmith with DVC point availability. Summer availability is as I stated in my first post, and even less then I expected. Point rooms in 2 bedrooms are definitely available as stated for late October and most of November with the exception of thanksgiving which is gone. Studios and one bedrooms are showing as much as 3 nights in a row.
The points rooms can not be converted to cash until last minute if not booked by member points. The other way for cash rooms to appear would be if someone uses points to book a cruise, adventures by Disney etc. Those are the best bet right now for cash rooms. But, using points for other options is such a bad value overall, that people just don't seem to be doing as much of it as the point price has eclipsed for these offerings.
But that market may be a bit sketchy for awhile as in members may not want to risk more cancellations and have their DVC points turn into reservation points which have limited use for activity other than DVC resorts. Once they go, they don't come back the same.
DVC has also stated that for the time being they won't use their points to compete with members for availability, which lessens the chances of rooms becoming available for cash.
So, best case scenario would be to rent points to secure a room. As
@disneybirds stated this has been a huge pitfall during the Pandemic, but hopefully for renters and owners alike, that will turn around.
I doubt we will see many cash available rooms at HH for October and November before September. Not saying they won't be there and that people shouldn't stalk the websites, but I wouldn't expect much before that.
For 2021 cash nights, I would start stalking at the 11 month mark for cash nights on the regular Disney website.
Oh and editing to add another point: One of the anomalies of using points at HH is sometimes paying cash is about the same as renting points. For instance a 31 point one bedroom in July might go for around $400 plus tax from Disney. But 31 points at $15 a point is $465 as a rental price. A 15 point studio in summer might go for $215 plus tax in cash but 15X $15 per point is $225. Plus - weekends are 27 points so yikes!
Point being, safer to rent from Disney as the savings don't justify the risk.
At Disney World the renting makes more sense as the room prices (without measurable discounts) are so much higher.
Now I must clarify that I haven't checked cash prices in about a year for summer.