We've learned the hard way to always leave extra cushion time before any dive trip, especially a liveaboard. It is not just because of delays and lost baggage but because we need the time to chill out and get healthy.
When we were younger we used to work crazy long hours just to ready to leave town, stay up all night to pack, head out to the airport before dawn, try to sleep on the plane, and stumble out to the dive boat (or house pier, or LOB) just as soon as we arrived at our destination.
It often happened that one or the other of us would get a head cold and that would lead to an ear infection and would cut short our dive plans. Now we allow extra time and enjoy relaxing in a lovely vacation destination before we go diving.
I think the best example of the importance of leaving at least a little extra time in advance came from
@Skittl1321 a couple of years ago. They had planned the "trip of a lifetime" to the Galapagos that included a day in Quito, Ecuador before boarding. It just happened that they were leaving home at the same time that all flights out of O'Hare were cancelled because a contract employee decided to kill himself by burning down the air-traffic control facility. It caused major cancellations and delays all across the country and internationally.
They were stuck in various airports for hours while scrambling madly to figure out a way to make it on-time or book an alternative trip to Mexico. They actually made it to the boat just before boarding but they would have missed it if they didn't have at least one day as a buffer. They had insurance so they would have gotten the money back, but they would have missed their "trip of a lifetime" and that would have been a major disappointment.
Regarding bucket lists, the Red Sea and Egypt was our "trip of a lifetime". I am so glad that we had that opportunity because I don't think that I would be comfortable heading back to that part of the world during the current political situation.
What a shame, we met many lovely people, saw amazing cultural and historical sites, and the diving was wonderful.