Pros and cons. There is no definitive answer due to so many variables. If you are retired or time is not the main issue or you like the mystery of not knowing where you will go this year, then your answer can be late bookings. If you need certain dates or certain PHs or special quota or have to ask off time way in advance (which is the majority of US workers) well you can see where that goes. The short answer is try to do both and see which fits you better. All depends on your situation and short or long term goals.