Wystan goes very well with Chester...Chester Kallman was W.H. Auden's boyfriend/platonic BFF. I've always been struck by how well those names go together. And you're right,
Chester is more of a place name than a surname.
Hollis, Wexford,
Clarence,
Wilkie,
Jarvis,
Eustace, Makepeace, and
Llewellyn are all so good.
Lowell is cool, and I love the nn Lowey (or however you would spell that). But
Lowell, Massachusetts is kind of a sad place!
Mycroft is outrageous! I love it. And of course his brother's name is
Sherlock!
Wilmot is neat. I'd never thought of it before. Now I'm off to go look up the
Wilmot Proviso and see if that's something worth sharing a name with.
As for family LNs, I don't have an awful lot of Irish/English names in my family tree, and those seem to make the best transition to the FN spot. There's Mountain (which I'd love to use for a MN...as a FN it's just "too much.") And Greenlee (which is getting trendy now! But I think it's obnoxious as a FN.) I also have Crowley and Gilsenan (ghill-SENN-an), which are both awesome, but they still feel like acquired tastes to me. I've kind of mused of using Aguirre (uh-GHEE-ray) as a FN, perhaps with the NN Gui (ghee). But people have enough trouble pronouncing that as a LN, so I probably wouldn't inflict it on a kid.