I typically begin to plan for the next season in the middle of the summer but I begin saving for it a little bit before then.
Same with us, we began planning for 2015 on Nov. 1, we made notes on what worked well, what needs to go, and what needs rework. Our list is pretty extensive already! Also, like UnOrthodOx we begin some building in the New Year. Our probelm is that it is very cold up here so we work on the smaller, more detailed items in the basement. Larger builds have to wait until spring as the garage is too cold.Nov 1, I sit down and make a list of what went well and what didn't. Nov-December, I'm usually researching concepts and coming up with a build or two I want to focus on. January, it's go time.