How many will he win? As many as he wants :bosstrips
I really don´t care about quantity, but quality of the reigns -If there´s a good reason (storyline/feud), and he can back it up in the ring, then I don´t see a problem with him getting it a few times more. Flair went ahead and disrespected the Business when he retired from WWE, so NOT surpassing him out of respect would be a joke.
I´d rather have him reach 17 title reigns that matters, than having Roman as champ for 5 boring, pointless reigns.