It's not that Cailyn looks uneducated, it just looks unoriginal amid the sea of parents who are finding it trendy, creative and 'cool' to tack on a random '-lyn' ending to an unsuspecting prefix. I honestly can't imagine a CEO of a company or a grandmother named Cailyn. (Of course, that will probably change in the upcoming years.)
What irks me the most about the spelling 'Cailyn' is that 'cailín' is already a word, a Gaelic word pronounced 'coy-HLEEN' and meaning 'girl' (it's the word from which the anglicised 'Colleen' is derived). The only analogy I can think of would be if a person that spoke a language other than English decided to name his or her child 'Girl', but wanted to use the spelling 'Gerl', and instead of pronouncing it 'Girl', pronounced it 'Geerl'.
While I'm not necessarily against using words for names, I prefer for the spelling to be kept in tact and for the pronunciation to be kept as in tact as possible, which understandably may vary a tad if using words/names from other languages.
Please understand that I'm not attacking you, just stating my opinion on the name. :)
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