Personally, I have found the best time to book is when it is a fare you can live with and that is regardless of the month, day of the week or time of day for booking. Fares do fluctuate but I do not buy into a lot of what is published as to when the best time to book is. With reduced options for most of the country, waiting will often result in a higher fare.

Like you, I could have driven 4+ hours to another city for JB but the parking and a hotel stay on each end of the trip wiped out any savings.

Refer to my earlier post in this very thread as to what has happened to the exact itinerary I booked back in May. Had I waited to book, I doubt I would be going now.