I’m sure DH will have more to say on this, but we just booked a June trip to Kauai and we obviously waited too long by booking 4.5 months ahead. We ended up paying for flights with cash because the only flights remaining that were available for points were bad times (red-eyes, 6AM departures (which are basically red-eyes when you think about having to get up at 3 to be at the airport at 4), etc). I can’t do red-eyes anymore, DD and I both need our sleep. Also, hotel inventory of garden view rooms (and garden view rooms available for points) was extremely low – we made some non-optimal choices and now we are having to pay some cash for the hotel instead of using 100% points. DH is upstairs gnashing his teeth as we speak.
Just a reminder – if you want to use points, book WELL AHEAD. We were going to book this summer trip right after the holidays but we got sick and the time got away from us. The economy is pretty good and obviously, destinations are going to be very full this summer. Don’t wait, book now!