Bringing Woody and Buzz back together could be an issue for Toy Story 5, but the solution could be found in Pixar's 14-year-old movie. The announcement that these characters would be returning for another movie was quite a surprise since Toy Story 4 gave the gang such a satisfying ending. It seems counterintuitive to pull Woody out of his "retirement" so soon, and having him reunite with Buzz after their heartwarming departure undoes the emotional impact of the last film. However, Toy Story 3 reveals how the franchise can continue without doing such damage.

https://screenrant.com/toy-story-5-woody-buzz-problem-time-jump/