Yep...... window closed. That's why I hate this timeline .... lots of guys get put in bad positions.
I am not sure when the portal opens again but it will be Fall/Winter. If I understand the new rules correctly, he could transfer anyway, enroll, then hit the portal when it opens to be immediately eligible to actually compete attached. NIL deal should be in place no matter what since it's not the school handing it out. He could also go in the portal Fall/Winter then officially transfer at the semester. He may have to compete unattached at opens in the beginning.