I LOVE this name, I want to name my son this. I am a little nervous about it though due to others seeing it as youthful/not professional. I will most certainly be calling him this as a nick name.
I personally love how unique this name sounds for a boy, and even a man. I don't really get the immediate connection to "Riley" because Wiley takes on a whole new sound/meaning in itself. While searching for unique and cool boy names I came across this one and think its pretty awesome! I predict it will make a comeback :)
Riley is becoming so popular, so I don't see anything wrong with using Wiley as an alternative. (for a boy only of course!) it's a cute, quirky name but I think it will age just fine. And as a bonus there aren't too many Wiley's around anymore, so it's quite unique!
A suggestion with this name is that if you have a girl you can name her Willow and then nickname her Wiley. If it's a boy, use William. This way they can change to their real name when they want to be taken that bit more seriously.
The trouble with any -iley name is that they'll sound a bit youthful on people in their 30s and beyond. At least Riley and Kiley sound better than this one, I don't like the 'w' sound. This sounds like someone with trouble pronouncing 'r' pronouncing the hideously common Riley. The name is very youthful and not very sophisticated.