If you want a guaranteed vacation I would never wait till the last minute. If you are having problems coming up with enough funds for a trip you might be able to score a trip but your chances are really slim. If you have 2 or more people I would not wait for a last minute trip. I have actually done a last minute trip back in 2012 on leap year from airfare on us airways roundtrip from louisville,ky 1 day park hopper 2 night at pop century all for $546.00 and I booked that 4pm and the flight left at 6am the next morning but i am single and no one else was with me. almost every other week I search for last minute trips like that and they are not coming up with them as much as they used too.
A little about me i'm 23 years old and i have been to WDW 26 times