I think the point being made about Serena was that the serenity is missing. I do think any sort of virtue or descriptor names are a risk - an ungraceful Grace or a short, stocky Willow. A blonde Raven, a really shy and unassuming Maverick or nervous Danger. Abel as mentioned up thread is a shock.
I know 2 sets of adult siblings called Michael and Michelle. Stunningly unimaginative. I also know of more than one family where the siblings are anagrams of each other, like Amy and May (but not) or alliterative siblings or "matching" twins.
I find misspellings odd, like why wouldn't you Google? Things like Pheobe, or Pheonix, Immogin etc. Names with a variety of legitimate spellings are trickier I guess. One DD went through a phase of being surrounded by Lily/Lillie/Lili/Lilly and I spent a lot of time checking before writing invites/cards.
DS played in a football match where the other team seemed to be all surname type names - Hudson, Baxter, Berkley, Cooper, Oakley. It seems a real naming shift especially among boys. Nothing necessarily wrong with any of the names, just a real shift.
When we named ours we went v traditional, family names, mainstream spelling etc. I know a lot of friends and family saw/see our choices as boring or unadventurous. Some openly said so, or that they pitied the kids. Mine are all the only one of their names in their school though, have no issues with spellings or pronunciations and no preconceived stereotypes to fight.
I've learned though, that however much you think you won't get used to a name, you do. They just become who they are and you use it. So while I do have thoughts, I never ever voice them.