hi lsyorke! i'm right next door to you in Westfield and we just bought into DVC in 2002. With 2 little kids, I only fly out of EWR and it has to be nonstop. That leaves Delta or Continental. We are planning a june trip too. The best I've seen for decent times is $211 (incl. tax). If you're willing to do very early morning or late evening out and back it comes down a little, but to us getting the kids up and out at 6am is no fun! We went EWR to MCO last sept which is not peak season and our rt was $189 (incl. all taxes), so all in all 211 is not that bad. I had booked that last Feb. The fare did go down a little ($15) after that but not for the flights I wanted. My strategy like yours is to check every day, but probably come mid Feb I'll book. As someone else mentioned at least from EWR the fare doesn't really go down that much, but can go up quite a bit.
If I spot something great, I'll give a post here