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Your target trip is Fall 2026. For September 2026 for example you would book October 2025 for it.

You would use points that at in the UY covering that trip. (If have a June UY, it is 2026 points. If you have a December UY, it is 2025 points.)

Also you look at how many points you have that can be banked from the prior UY or borrowed from the next for the reservation.
When I bought I thought I wanted Oct use year because I do t want to go when Orlando is on fire. I settled for September because the contract was kind of what I wanted. Turns out I am happy with that and have a trip booked for the end of Sept which is the cheapest time to use DVC points. Nevermind Orlando will still be on fire.
 
For your UY, you've identified the months you are MOST LIKELY to travel to WDW - September and mid-summer (I'll just say July and August for that). That is part of picking the best UY. To pick the best UY for you, you also need to consider the months you are LEAST LIKELY to travel to WDW. You want those months to come just before your UY begins.

So, if you think you will almost never travel during November and December, then I'd probably look at a February UY.

If you think you might want to travel around the holidays or the winter months, but you're definitely not going in late spring (April/May), then you might want to look for a June UY.

What you want to avoid is (1) ever having to cancel within 30 days of a reservation no matter your UY, or (2) canceling a reservation in the last 3 months of your UY, but even with 30+ days notice. If you do #1, no matter when, those points go into "holding." If you do #2, they won't go into holding, but you will only have to the end of that UY to use them or lose them which can be as bad or worse than points going into holding.
 
So if I buy a contract with a UY in February, and no points left in 2025, will I be able to book my September trip before the February points are available? Like I would want to book my trip in October of 2025 for September 2026.
 
So if I buy a contract with a UY in February, and no points left in 2025, will I be able to book my September trip before the February points are available? Like I would want to book my trip in October of 2025 for September 2026.
Yes.

If you choose a February use year the 2025 points would cover trips between 2/1/2025 - 1/31/26.
September 2026 would use the February 2026 points. If any points were banked from 2025 it would use those first.

It doesn’t matter if you have points at booking only that they are available when your trip occurs.

If you wish to book somewhere that requires 100 points to stay on 9/1/26 you can book it on 10/1/26 if it is at your home resort and you have a total of 100 points in the Feb 2026 use year. It doesn’t matter if you have a 100 point contract, or a smaller contract that you have banked/borrowed points into as long as you have the 100 points in the Feb 26 use year you would be able to book the reservation. If this trip was not at your home resort you could book it subject to availability on 2/1/26.
 

So if I buy a contract with a UY in February, and no points left in 2025, will I be able to book my September trip before the February points are available? Like I would want to book my trip in October of 2025 for September 2026.
With Feb UY (in fact any UY wanting to book Sept 2026, books Oct 2025) would be using 2026 points. If there are no 2025 points, you would only have the 2026 and points from 2027 to borrow.
 
If looking to purchase a Feb UY contract with the Sept 2026 date in mind, it would be beneficial to have as many 2025 points as possible. (With the length of time it takes from ROFR, closing, and membership established, I’d ask seller to bank those 2025 points since you most likely will miss the Sept 30 banking deadline).
 
So if I buy a contract with a UY in February, and no points left in 2025, will I be able to book my September trip before the February points are available? Like I would want to book my trip in October of 2025 for September 2026.
Yes. :)

It’s a 11 month window for your trip. It only matters that the points will be available for the trip, no matter when you do the booking.
But you will want to book as close to 11 months ahead as possible for your home resort, and 7 months ahead for any other eligible resort.
 















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