Hubby and I had a little fun debating this one. Nice question!
Our conclusion was the Jewish neighbor from New York.
The Mormon and JW are the easiest. They are there at your doorstep to convert you. The entire conversation is around converting you.
Converting them just depends on how much you know your faith and theirs. You can plant bugs in their ears that aren’t easy to get rid of.
Plus…they can either run away and not come back, come back and bring reinforcements and continue the discussion (more opportunity to plant bugs) or they can convert.
The Muslim from work is tough just because he is a coworker and that isn’t the best time or opportunity to convert a coworker.
The Cafeteria Catholic shouldn’t be too hard at all…as long as they are on the same level playing field when it comes to Jesus. Even then…if they are willing to listen to you and have a discussion about the Church.
I was a Cafeteria Catholic and my husband was a protestant that convinced me of the validity of Catholicism. He and I went through RCIA together…

As long as the Catholic wishes to engage in dialogue…you can either convince them of what the Church teaches or try to convince them to become an Episcopalian.
The hardest is the nice Jewish lady. She is your neighbor, she is from New York and she is at least culturally Jewish. Therefore you will have conversations with her, she will be stubborn and you will have a ton of history and tradition to erase from her in order to convince her to become Catholic.