Nothing wrong with long range planning, as long as you're flexible about needed changes. Trip insurance needs to be purchased right after your first paid deposit to cover preexisting problems. Your airline is the most likely to change things. The piers will probably still be there, as will your hotel and dive op, but changes are always possible.
I planned my Solar Eclipse trip over two years in advance, finally got serious about details six months out or so when my kids committed to their travel days & preferences, got new credit cards with the airline to save bags fees, and watched fares with the one airline that could handle our needs - gave up on returning from Idaho Falls as too high, and selected a return from Bozeman that left late enough for us to be on the totality line for the event, then drive to the airport, if nothing went awry. We absolutely had to be back that night, or at least accept the risks.
Then the airline canceled our return flight a couple of months out and wanted us to leave before the Eclipse! Totally unacceptable. I kept an airline agent on the phone looking for other ideas later the same day for quite a while, politely whining some, and then suggested I could leave from Idaho Falls. He got it approved! We ended up driving less and leaving from our preferred airport for the lower rate after all.
Then we got delayed leaving Lubbock as the pilot watched a storm in our path, arrived in Denver too late to make our connection, and looked to see our next plane parked away from the gate waiting to go. I never understood how my daughter got them to reopen the doors and pull the stairs up to the plane, as airlines just don't do that - but she did. Out bags even made it.
Hotel Plaza gets good reviews on my favorite booking site, and they are booking that far out. I hope you booked a refundable rate in case of changes. I have to wonder how often people fall off of the rooftop pool deck?
