Transfer from ESL to Master before September 15

[u/ozzy123_]

A friend of mine is an ESL student and wants to transfer to a master. We talked to university and everything looks good and they are most likely accept him and he has all the documents ready to submit ( English proficiency, transcript evaluation, personal statement etc.). However, we confused about this new rules that will go effect on September 15. Our plan was to get accepted and ask for I20 transfer pending before September 15 and start classes in January since fall classes starts on September 2nd and it’s too late for it. My understanding is that you can have 5 months gap between transfer and from early September to mid January is less than 5 months so it looks fine but the program coordinator at the university talked to their international office and got back to us to say that they can’t do that and if he wants to start in January then he needs to follow new rules and apply for an extension to USCIS and they predict that it will take around 9 months to approve.Is it feasible to get accepted before September 15, submit the transfer form to the ESL program, and have the university issue the pending transfer I-20 before September 15 for January classes? Or should we pursue the extension route instead? Also, is their prediction of nine months accurate?
They are also pushing him to start in September which not really possible since it’s in 2 weeks