I don't think he would be using an iPad to preach. In his life, people approached him without much preaching done, meaning the Sermon on the Mount was his biggest event. (Correct me if I'm wrong.) People approached him for healing themselves, their sick family members and others, and for meals from a boy's few fish.
Today, Jesus would have a more direct media than JW.org. Jw's think this is the ultimate; the society has a website. Big Deal!!! He probably would have a more direct media like Joel Osteen, satellite TV, and radio. Or, since everyone has smartphones, to send a message of hope when you are having difficult times, sending a text message just before you sinned, etc. I have to laugh at witnesses trying to impose their current habits into scripture based precedence like the early church members had book bags. Riiiiiight!
I wonder if Jesus would use Twitter or Instagram or any of the other apps to further his preaching work. Seems, he has personally been silent for 2000 years. However, if you want to consider other avenues than JW.org website, or their not at home to not at home then to Starbucks coffee work, or useless advertising with the carts while they use their smartphones while ignoring everyone, God is here every day in our lives.
If WTBTS owned an airline like Lufthansa, Jesus would have flown it exclusively. If WTBTS was a hotel owner, guess where Jesus would have stayed, in a manger? No, the approved WTBTS list of approved hotels. I guess he would have used Uber to get him locally from one place to another, all the while sending updates on Twitter, Instagram, Facebook, and we could go one but you get the idea.
I believe the WTBTS organization has truly lost their sense of direction, trying to point to themselves all the time and how they alone are God's sole channel to mankind in these modern times. If God does have a direct channel of communication to mankind, I hope they are on the right frequency, because it doesn't seem so with WTBTS. Just Saying.