How Bernard knew what to say
It wasn't just Sutcliffe, Blenkey and Armstrong that Bernard wrote to. He also wrote to Ian Brady, David Copeland (who he assisted in the conviction of), Marie-Therese Kouao, Roy Whiting, Ian Huntley and Maxine Carr, Michael Stone, Tony Jasinskyj, Tracy Connolly, Vanessa George, Darren Newton, Mark Shirley and Kenneth Erskine, to name a few.
Having spent time in prison himself (and being associated with The Essex Boys) he has a deep understanding of what inmates go through during there time there; and how to exploit these feelings and emotions. What most inmates want, especially when they're imprisoned for something people are generally opposed to such as murder and child abuse, is just a friend and someone who believes they're innocent, which is what Bernard provides them with.
This can sometimes be what causes those in prison to fall in love with Bernard's personas. They see their pen pal as someone who truly believes their false innocence, and see them as their only companion in their dark time, so they begin to rely on them as they're essentially the only thing they have left in the world. So you could imagine the disappointment when the love of their life - in some cases the lady they had proposed to - turned out to be a middle-aged man.