I would love that to work. I wish anyone the best of luck attempting it. However, I do not think there are many examples on this board of JWs being directly 'reasoned' or 'argued' out by an external influence. In my experience presenting a challenge to an indoctrinated person is nearly always viewed as a 'test of faith' an opportunity show off their spiritual qualities.
Obviously you might have results with someone experiencing doubts or someone already looking to leave. IMHO for someone to help a JW out of the Borg involves creating space between the follower and the organisation.
I expect many have researched this personally and discovered the 1914 date issue and I believe that is different. If a member is looking for inconsistencies in the faith, they are probably already drifting away.
So I suppose my concern would be, at worst, attempts to argue doctrinal matters could potentially strengthen the faith of some. Of course... you can lead a horse to water...
Anyway, if you do get the chance to discuss this with a JW let us know what happens!