No registrar I've used will let you transfer an expired domain. Some even prohibit you from transferring a domain for 60 days after a renewal.

I'd go ahead and pay at the old registrar and find out if they have a waiting period after renewal.

I just got dinged on a bunch of EU domains I was planning to transfer that weren't even due... bastards at Dotster renewed them 45 days early at a rate about 3 times what Enom charges.