@Lemonslice this is really helpful as those were all my concerns as well!!
He is a full time graduate student online but also does medical documentation remotely.
We are thinking to avoid any issues to just reduce his trip to 5 weeks (he has all his vacation time left) . And then check his i94 online once he gets here to see if they grant him more time (awesome if they do, but okay if they don’t). Would that be reasonable?
OR he can drive via land border as they’re usually much more relaxed and give him more time.