He listed about 15 topics for us to study, to prove only JWs are based on 1st century Christianity. I got him to agree not to attack other religions, (proving them false does not prove JWs true)
What points was he using to attack other religions? I remember the ones that were being used as I was growing up, slagging them off because of how many people were leaving, getting involved with politics/un, scandals involving the church/catholic child abuse scandal, believes not standing up to scrutiny, etc. All of these can be turned around to show exactly the same applies to the jw's.
if he's the typical jw then he'll give you the whole "you must first take milk before solid food" spiel. he will want to cover all the basics with you in order right in the book
If you push him too hard he'll class you as apostate and stop the study with you, giving you even less of a chance with your friend. I would let him follow the subject he wants to follow each week, but research each subject so that you have all the right answers ready. What book are you studying and where abouts are you up to in it? Perhaps we can give you a few ideas.
Expect your study conductor to bring an elder with him next time to help him with your difficult questions, so there'll be at least two people facing you next time. Don't forget I live close by if you need any help.
Paul