Re: How can I reduce excessive worry about name associations?
It just depends on where you live and what sticks out to you or most people.
Most people wouldn't think "Jeffrey Dahmer" when they meet someone named Jeffrey.
Alexa and Hillary are common names and very usable.
If you want a name with zero associations, you'd have to make up a completely new name that no one has ever heard before, which is almost impossible if you also want the name to be usable. Any name that's been around for a while will always have a past. It's up to you to decide what you think is a dealbreaker.
Also, even if you do find a name without any obvious associations you'd want to avoid, you could name your kid that and then 5 years later someone else with that name is in the news for something. You can't predict what names will be culturally relevant for good or bad reasons in the future.