Yes.
For example, if you had a December use year and wanted to stay 11/29 - 12/5. You would book the nights of 11/29 & 11/30 from the 2018 use year points and 12/1 -12/4 nights from 2019 use year points. Taking points from two use years for the same reservation is apparently beyond the capability of at least the online booking system. So you would book a reservation from 11/29-12/1 online and then call MS to book the rest of your stay. Or you could call MS to do the whole thing for you, but MS opens one hour later than online, so in some circumstances, you would be shut out and have to wait list.
I believe MS can link the two cross-use year reservations, but not combine them into one. Combining is preferred because it appears to the resort as one continuous stay and there is no chance you would have to check out and back in again between the reservations. If the reservations are linked, you should not have to change rooms but you may have to go to the front desk and check out and back in again. This is inconvenient and could also complicate dining plan usage.
More importantly, straddling use years can prevent you from "walking" your reservation online (due to banking and borrowing rules). That's a significant disadvantage if you are trying to get a studio (for most WDW resorts) during the popular periods (mid-September - Marathon weekend, race weekends, etc.).
So get a use year that is at least one month prior to your usual vacation time - if you travel at the same time of the year on a consistent basis.