Apply for student visa - special scenario

I write this on behalf of a friend:
He plan to arrive early next year to study continuesly chinese at a approved school until
around september. Then he will start his chinese university program in a different city -
getting his master degree …
He prefers not to leave Taiwan for Visa purposes, is it possible.

For example:
Apply for 60 day extendable visitor Visa and fly in e.g. Februar 1st.
Around End of March first 60 day extension
Around End of May second 60 day extension

Around end of July / early August he has to apply for his resident-visa and
then for ARC.
Pay student-fee until the semester will finish in September, regardless he may
miss some weeks of them …

As on all visa and his ARC is the name of the language school written on, is it
possible to change his ARC card towards his (from September onwards) new
university-name ??

Or does he has to fly out to apply for a new visitor-visa and make the whole
process again ?? If so, what does this mean for his health-insurance ??
Would it start from his first ARC or the 2nd one (around 7 months later) ??
Could he not just continue to pay his monthly fees directly over 7/11 ??
(well, after September he can pay the bill at old school anymore …)

thank you