I plan 2 years in advance. I'm not so much anal, as I am excited. When I leave WDW I need to know when I am coming back. Obviously I have nothing booked yet, but I know where we are hopefully going to stay in 2015 and 2016. We do Easter break when they fall within a year of each other since that gives us 10 days of school vacation each trip, and the ability to use an AP. If things don't end up going as planned, I don't care, but I love to plan it! Just like ADR's, those are 180 days in advance. You can chose to not book 180 in advance but then don't be upset when you can't eat in the castle...
I'm like you. I love to always be planning some trip. We go on a cruise in 3 weeks and that's all set...we do F&W in Oct and that's all set...we even have everything set for Xmas at WDW with all my inlaws. I need something to plan, so it's next year's trip. We know that Aug will always be a family trip, so in Sept I'll book Aug 2014 at HHI. I'm kind of in limbo right now with nothing to plan...so I just booked MIL and FIL a Bermuda cruise for them (with gift certs that we all, DH and SILs, have been giving them for the past 18 months). Hurry up Sept, so I can book my next trip.