If you book a package you only stand to lose the deposit of you have to cancel prior to eight weeks before check in. With DIY I used to get insurance once the flight were booked so it's true in part that you should be covered as soon as possible, but depending when and how you book, not necessarily immediately urgent. I didn't like to take put insurance until the our flights were booked because if we needed to change dates before then, there would have been an amendment fee for the insurance cover. You need to assess all aspects. Not all trips are the same.