If you add on through Disney, you WILL get the same use year. If you add another contract through resale, you can choose your use year. Frankly, even with 3 contracts with the same use year, I can still mess things up with different resorts. I'd keep it as simple as possible unless your use year really is a detriment to the time of year you travel. Of course, that being said, our use year is probably the worst we could have for our usual travel dates, but in 12+ years it has NEVER been an issue.