I am a planner and tend to schedule far out in advance.
On the books so far we have -
Jan 2018 - 3 Nights in WDW - ($800)
July 2018 - 6 Nights in WDW for a Youth Baseball tournament at the Wide World of Sports - ($1040)
Sept 2018 - 11 Night Disney Cruise - Dover, England to NY ($6000 for the...