What is going on with SEPTEMBER?

Yes, this is exactly what I'm doing. Thank you for the advice.
Good Luck - I am in the midst of doing similar for a Disneyland Trip in June and WDW trip at the end of November.

For the Disneyland Trip (Our First), we have a cash stay already booked at the Grand Californian with a waitlist active for the same dates (Hopeful, but not worried about it as much). For WDW, we have our room booked at Riviera already on points, but hoping for another room type to pop up on another waitlist.
 
I will say, that the majority of the North Easterners, who aren't used to satans temperatures, don't tend to travel to Orlando in the summer months. Obvioulsly one must travel when the kids are off- but I know of all my friends, no one wants to be here.

NYC can be just as hot and humid in August as FL at times, and without the benefit of those pm thunderstorms that sometimes cool it off. A lot of my family trips growing up were around that time because we went back to school later than most of the country (September). It was really no worse than being home, except the hurricane threat.
 
I think the DVC "slow" and busy seasons surprise a lot of people when they start researching. It did me for sure. DVC owners are point misers in general, so it's busy when points are low, and that's during the traditional slower park crowd times.

As for September weather, I get it's still hot, but we find the last week of September you at least have a chance of it being not AS hot and humid as July and August. Even of its 90 but the humidity is cranked down a bit, I can definitely feel the difference. And I live in Alabama so trust me I know heat and humidity. 🔥
 

In terms of DVC, September is the least expensive (i.e. fewest points per night.)

Also, Food and Wine Festival is now in full swing for the entire month.

As a result, September is popular among DVC members.

In terms of overall difficulty to book DVC, I’d say August is the easiest followed by July.
We used to visit in August due to school schedules, and never had much of an issue booking even at the last minute. We‘re visiting in September this year (have done that a few times before, including last year) because we have a few non-Disney trips planned and have points to use. It can be pretty hot, but we try to keep our plans “reasonable” in terms of not pushing ourselves too hard, but we’re not traveling with kids either. I didn’t have too much trouble booking a one-bedroom at BRV (we’re excited to see the renovated units), but that may have been luck more than anything else.
 



















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