I never thought of it as old-fashioned, but I guess it is. It's one of my favorite names ending with -land. The Cleve part isn't nice by itself, as it reminds me of Cleavage (which is a surname, but has come into modern usage as 'breasts'). I don't think that a kid called Cleveland would be picked on for it though, and you don't have to live in Ohio to use it. It's not just a place name. It's a surname, and it hasn't gotten snatched up by the surnames-as-first-names trend yet. Perfect. :D.
City names are plain weird. What if the guy hates the place when he's older? What if you have to move and the kid has to live in a place where people hate the city? Besides, this name is old-fashioned big time.