I would not rely on "bundling" these separate CD IRA's, hoping to pass the once a year direct rollover by the owner. I would have the transfer done Trustee to Trustee. It should be foolproof that way and leaves the option for the client/owner to do a self-directed later in the year if desired. Whomever the recipient is should be able to work seamlessly with the current holder. He may take a ding on his earnings since he is cashing out early, but like you said, no penalty involved, and a promise of better APR and returns.