New Snowbird Asking For Guidance

rk911 wrote:
Looking for some guidance from experienced snowbirds.

Up until now my wife and I had to spend winters at our home in west suburban Chicago. We have been able to leave Chicago around March 1st and head to Mesa, AZ for at least part of spring training. That has changed and we're now able to spend much more of the winter away from the cold and snow but we still have a few family commitments that will require us to stay home until roughly January 10th. We're trying to plan this as best as possible without having a date certain when we can leave home as weather at home will play a huge part. It's not so much when we can leave Chicago as it is IF we can leave Chicago as planned.
If reservations are needed must they be made months in advance or are the parks full of others like us meaning making reservations now? But if we can't lock down a departure date from Chicago how can we make reservations anywhere with the certainty of an arrival date? Bad weather that crops up along the way can play havoc with a schedule.

How do you experienced folks deal with that?