August 2012: Wife, 3-yr old daughter, 6-yr old son, and mother-in-law
April 2013: Wife, daughter, and son
January 2014: Wife, daughter and son
We live in Pittsburgh, PA and make the drive in 2 days.
We've pretty much agreed that we'll make the Disney trip on annual basis because for $2500, nothing really beats it. Last year, we did go to Outer Banks for a few days over the summer, visited Lake Erie for a weekend, Kennywood (local amusement park, which we got season pass for 2014), and some other local parks like the Laurel Caverns to walk through a cave and some historical sites like Bushy Run Battlefield and Fort Necessity.
The great thing is hopefully being able to mix in other short trips around it to not make Disney the only thing they experience with the family.
This year, we're planning to do Disney in January, Gettysburg in the summer after school is out, Kennywood, Lake Erie, and depending on family commitment, going to a wedding in Boynton Beach (which I probably will surprise everyone with a day stop in Orlando to go to Disney - lol).
I hope everyone can afford to go as often as they would like, be it a few times a year, annual or every few years.