This was our first experience with Holland America and our second trip to Alaska. My wife and I have been on three other cruises, two with Princess and one with Carnival.
I blame myself for the initial stress I experienced since I didn't realize my wife's passport had expired and I was concerned that a driver's license and birth certificate wouldn't be enough for her to fly and cruise with. After some phone calls and web research I was assured we would be fine since we were sailing round trip from Seattle but I couldn't relax until we were on the ship. As it turned out, everything went smooth as silk, even when entering Canada, and I was able to enjoy the trip.
I booked my own plane tickets out of Detroit and opted out of the HA transfer to the pier hoping to save a little money. A little research after the fact showed that a cab ride was about six or eight bucks less and you had to handle your own bags at the pier. When we got to Seattle we went to the HA desk, bought transfers, handed them our luggage and got on the bus. Worked out just fine. Not only was it worth a few bucks more to forget about the bags until after we got on the boat, the HA people made sure you got to where you needed to be with minimal hassle.