Aside from the obvious Romeo & Juliet connection to me it just makes me think a 'Romeo' is a bit of a stud/ wanted by all the girls, a bit of a player etc. I think that unless your son is guaranteed to be rich/ famous (eg: Romeo Beckham) it could be a hard name to carry off. I could imagine a popular, handsome boy the girls all fancy managing to pull off the name Romeo but for an average boy, a boy who isn't a typical 'lad,' an academic boy etc it might lead to teasing etc.
If you like the Ro sound how about Ronan, Roman, Roland or Rowan? Or if you like the eo how about Leo or Theo?