A very thought provoking question. I have had many "new" chapters some of them came at the end of a happy previous chapter and others occured through transition, illness, death and professional or personal circumstances.
For me enjoyment, which is definitely something I always hope for and seek, is usually influenced by how or why the new chapter started and what other permissions I have to give myself.
Sometimes enjoyment is bang, right there at the beginning, other times, it's a part of the process of adjustment and creeps up on me slowly. Other times it's not until a later time that I see there was enjoyment during that chapter of time.