1. Would a June '08 female be ready or is that really stretching it? (Probably stretching it but thought I'd ask anyway)

I wouldn't count on it.

2. Would an adult female that laid eggs this season be ready for the '09-'10 season or does she need a break?

Some people breed for 2 years in a row with one year off. Some people like to give them a year on and a year off.

I've also heard that most adult females when they have their environments changed (shipping), will most likely not breed that year. I've always wondered about this though; does anybody have personal experience with this?