Doing the trill (or roll as I call it) for that long is only a matter of practice. The most important thing (as always) is to relax.
Personally I'm not a fan of Will Wilde's harp playing at all. In everything I have heard him play, I haven't had any feeling of him putting any real feeling into it, or feel that he is particularly enjoying himself. It's almost as if he is simply going through the motions to me. Live he may be different, but I'm not enticed to go and see him by what I have heard on recordings at all.
I like Will Wilde - although Kingley raises some plausible concerns, I haven't seen many young people in this neighbourhood (i.e. Britain) who play with Will's ferocity and technique.
I'm not a huge fan of his singing, though. I reckon he's at his best when he's backing up his sister Dani.