There is certainly a wealth of book regarding apologetical arguments to use with Protestants. Some that help you get across these arguments at the personal level. Devin Rose’s new book Navigating the Tiber: How to Help Your Friends and Family Journey Toward the Catholic Faith combines both of these aspects.
I really enjoyed how this book was laid out. The first chapter addresses the fact that Protestantism in not monolithic in any way. So it is important to have at least a general idea of the beliefs of the major branches of Protestantism. One branch of Protestant theology might be at odds with a specific aspect of Catholicism while will either practice or be close to the same belief. So when talking to someone you have to have some idea where they are coming from and what their specific nuances are.
Most importantly one of the underpinnings of this book is being in relationship with people. He describes several of his experiences with co-workers in getting to know them. It was only in getting to know people that he was able to decide when to broach subjects regarding religion or whether to broach the subject at all. While reading this I was thinking of the phrase used in apologetics “Win an argument, lose a soul.” This book is very aware of that pitfall and he references conversations he had over a period of time. There is always the pratfall of Biblical ping-pong slinging verses back and forth and point-scoring. So there is also prudence involved in knowing a conversation just is not going to be fruitful for either party.
Along the way the book builds on fruitful avenues when working with Protestants and some of the typical blindspots. Lots of solid apologetic material. Again though the strength of this book is relationships and how to have conversations on these subjects that actually brings light instead of heat.