Plan Ahead. Way Ahead

I am the type who likes to really plan ahead. When there is a conference or an annual event, sometimes the philosophy is to wait for a last minute hotel rate. That only works part of the time. Nowadays, you cannot often do that when embarking on international travel. The more notice you have, the earlier you should book, especially if you are going to a very far flung destination like Sydney or Melbourne. 

HotelClub offers accommodations up to 12 months in advance.  One may not want to think abut what they are doing next year, but the time flies by faster than one may think.  There are annual events in New York City that it only makes sense to think that far ahead. Just try to get a hotel room for New Year's eve right now.

The other consideration is that people going to a smaller scale event like a wedding or a family reunion neglect to check what else is going on in town at the same time. Some relatives of mine ended up taking a trip while the Super Bowl was in town. They weren't football fans so they were totally oblivious. If only they had checked, or more so, booked way in advance, they would have had a reasonable place to stay.