I just checked the popularity of the three names on the 2022 Social Security website for the state of Massachusetts. [name_u]Henry[/name_u] is #4 or 5. [name_u]Everett[/name_u] and [name_m]Oscar[/name_m] do not even make the top 100. Personally, I would pick [name_u]Everett[/name_u]. I love the combination of [name_u]Everett[/name_u] [name_u]Duke[/name_u]. It is such a handsome name, can be shortened to Ev or nicknamed [name_u]Rhett[/name_u]. [name_m]Oscar[/name_m] is a little too out there for me. Also, think which is more your naming “style” if you were to have other children and needed to come up with names that worked well together.
[name_u]Everett[/name_u] [name_u]Duke[/name_u] would be a great name!
Team [name_m]Oscar[/name_m]! 
I love [name_u]Everett[/name_u] [name_u]Duke[/name_u]! For what it is worth, the only other [name_u]Everett[/name_u] I knew was in Massachusetts and I don’t think anyone ever gave his name a second thought regarding the city.
[name_f]My[/name_f] second favorite is [name_u]Henry[/name_u] [name_u]Duke[/name_u].
As an expat raising my kids in Latin [name_u]America[/name_u], my advice is don’t underestimate the value of an international name. Obviously we can’t name our kids with every contingency in mind, but I sure wish my parents could have known I’d fall in love with [name_u]South[/name_u] [name_u]America[/name_u] before they named me [name_f]Brittany[/name_f] 
[name_f]Amanda[/name_f], [name_f]Sara[/name_f], [name_f]Laura[/name_f], Stefani… so many 80s names would have been better.
So my vote is the gorgeous [name_m]Oscar[/name_m]. A name like that could serve him well anywhere 
In general popular names now are given to a smaller percentage of kids than names of the same rank decades ago. If you really love [name_u]Henry[/name_u], even as a popular name it might not be like it was for you as an [name_f]Amanda[/name_f] in the 80s.
[name_u]Everett[/name_u] does make me think of the place since I have spent so much time in and around there, but if you aren’t in [name_u]Everett[/name_u] or one of the nearby cities or towns I think it would be ok. I like the name a lot, maybe the most of the three, but I do think it [name_u]Henry[/name_u] and [name_m]Oscar[/name_m] flow better with [name_u]Duke[/name_u].
I don’t think [name_m]Oscar[/name_m] is too “out there,” but it isn’t my favorite in terms of the sound. That is fully a personal preference, though, so if you like it then I think it is a good choice.
Unless you’re naming your kid one of the many names that rhyme with [name_u]Aiden[/name_u] or [name_f]Addie[/name_f], [name_f]Maddie[/name_f], [name_u]Allie[/name_u], or [name_f]Lily[/name_f], I wouldn’t worry too much about popularity. [name_u]Henry[/name_u] is a great name!
I named my son [name_m]Benton[/name_m] and I’m from Arkansas! Bentonville, AR is where Walmart headquarters is located. 
There’s also just a [name_m]Benton[/name_m], AR and a [name_m]Benton[/name_m] county in Arkansas. He’s named after his great great grandpa on his dad’s side and [name_m]Benton[/name_m] has many more awesome associations in TN (where Hubs is from) than in Arkansas, so we went for it. People in Arkansas do give us odd looks from time to time, but we mention the family connection and his name is completely accepted after that. I wouldn’t worry too much about using [name_u]Everett[/name_u]. It’s much more commonly used as a given name than [name_m]Benton[/name_m]. Most people will think nothing of it.
[name_m]Oscar[/name_m] is a fantastic name! It’s absolutely not too out there. Benton’s middle name is [name_m]Grover[/name_m]. 
[name_f]Sesame[/name_f] [name_f]Street[/name_f] ftw! lol I also have an [name_f]Arwen[/name_f] which is even more out there. People are occasionally caught off guard by it and will ask questions about it, but most will just say, “oh what a pretty name!” whether they actually think it’s pretty or not. lol [name_f]Arwen[/name_f] went through a phase of wanting to be named [name_f]Sarah[/name_f] when she was about 4-5, but now at 10 she’s completely outgrown that and loves that her name is uncommon.
Non-US views. I love [name_u]Everett[/name_u] [name_u]Duke[/name_u] & [name_m]Oscar[/name_m] [name_u]Duke[/name_u].
I’d need to know more of why you maybe hesitant on using [name_u]Everett[/name_u] as a name due to the place, if you’ve no bad memories and it is not a well known town I doubt many will think he is named after or for it.
One of my favourite names (Elliott) is a favourite because of a place where I live (it’s a stunning beach) so I guess it depends on your why not/why for.
[name_m]Oscar[/name_m] maybe uncommon but definitely not rare or odd for it ti be seen/used, it’s a well known name (same with Everett).