I have never booked any specialty dinners prior to boarding ever and somehow I have always managed to eat around 2-4 specialty dinners every 10-21 day cruise
A request for a $20 tip ? We always have great service and tip way more than that. I have never had a steward beg for a tip and would be a turnoff. Mostly they ask to be given good grades on the survey
Back in the days of traditional dining we attempted to take different seats for that same reason and another cruiser got very upset “You are in my seat”
It all depends on personal preferences. Some like midship some like aft etc. We personally like aft so we would want to stay there but others prefer mid.
Princess does have a shuttle and then your bags will go straight to your room from the shuttle. The only thing that would stop you from getting there on time would be a flight delay or cancellation. We no longer take the risk and always come in a day early