My thoughts on your questions:
1. Not a huge fan of naming girls traditionally male names. At worst it just causes massive confusion (a girl named, say, Thomas, will have to respond to millions of calls/emails etc by correcting the gender.. what a pain). At best it just sounds kind of part of a small-town suburban trying to be cool trend (Casey, Riley, etc...). This was in vogue with urban educated parents say 10-15 yrs ago, but now just seems a bit dated as a fad (like the surname as first name McKenzie, Madison, etc trend). It's not terrible, it's just a little blah.
2. I do think others' perception matters to an extent. I assume most parents want their children to succeed and end up better off and more well educated than they are. So it makes sense to pick a name that will fit in well not only when they are little in their neighborhood but also if they end up attending a top university, being a lawyer/doctor/politician or similar. I'm not saying parents shouldn't be inventive or abandon a name they love in favor of something super-generic just to avoid any possible criticism/raised eyebrow. I just think whatever the trend in your local neighborhood, it makes sense to pay attention to whether nationally the name is considered trashy, overly trendy etc etc... so that the child can feel confident that they aren't prejudiced by their name no matter what they want to pursue as an adult. Of course a great child can overcome any name, but why give them something that just sounds trailer-park like?