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I think Raelle is too similar to Raina.
Raina is kind of nature-y, so less common nature names seem like a nice option for you. Skylar/Skye, Sage, Wren, Briar.
Just based on style & sound, I'll also suggest Isla, Lainey, Ayla, Dalia, Aria.
You may want to broaden your scope just a bit for boys. Synonyms for kind/compassionate or words with related meanings could lead you to more names
For example, kind & gentle are often used together, and gentle leads you to names like Gareth, Clement & Kevin. Kevin is actually made of elements that could mean kind/gentle/handsome + born. http://www.behindthename.com/names/gender/masculine/meaning/gentle
The word benevolent also comes to mind, there are a lot of saints & other religious leaders known for benevolent works, perhaps you could find inspiration there?
I am not generally a fan of Scout as the given name. Hazel & Caroline seem too feminine & traditional next to Piper. I don't care for Josie as a given name, though it's not bad with Piper. Selah is nice, despite it's long history, it's not as classic/traditional as some of your other choices, which I think makes it work well with Piper.
Oliver & Everett seem too proper/stiff/traditional next to Cash. Cash strikes me as very spunky and modern. Rhett is a great match for it. I also like Duke with Cash, if you are willing to consider moving it to the first name position.
Jack S. is very unfortunate.
I know the OP didn't want suggestions, but if she can get passed the popularity, Jackson or John could be a way to avoid the Jack S problem. She could still use Jack as a nickname. If he happens to have another Jack in class one year, simply instruct the teacher to use the full name instead of Jack S. Odds are, he won't have another Jack in class every year.
I agree with Emerald Bee, Lillian seems like a great compromise between Vivienne and Lilly.
If you like Nora, maybe Lora or Laura?
Lea, Lyra, Lilah, Luna.
For non-L names, maybe something with an L sound? Isla, Isabelle, Molly, Violet.
Since Logan & Liam both have Celtic roots, maybe you could sell you husband on a Celtic theme instead of the L theme. Fiona, Maeve, Keira, Alana, Ainsley, Carys (Molly and Isla would also work here).
If the legacy middle name is meaningful to you (and it sounds like it is) then issues of flow with first name are secondary. How often will he actually use his first & middle name together anyway? It's pretty much limited to graduations (sometimes) and weddings. If you aren't sure, I'd suggest taking a break. Sometimes some time off can provide enough distance to make the decision easier. Or, just consider the middle name set as "John" and then decide between Levi & Joshua once you meet him.
Joshua John is snappy, and does offer the nickname J.J. if he ever wants it. Joshua is a nice, classic name. It'll be familar to everyone but it's not super common among young kids.
Levi John is also nice, I think my only concern (and it's a minor one) is that Levi John sounds a bit like Levi Jean. Again, this is minor as he won't be called Levi John on a daily basis. Levi is quite a bit more popular and fits in well with the current Biblical name trend (Noah, Levi, Ezra, Adam, etc). You'll likely run across other Levi's, but it's not a top 10 name, so I doubt he'll be one of 5 in class.
I can't help you with the popular name issues, as my name was barely in the top 1000 when I was born.
My son's name is top 11 for the year he was born, and it was top 5 for our state that year. We really haven't encountered too many others-maybe about 3 or 4 I think. None of them were in his classes at school either, so the first name + last inital issue has never been an issue. I think it's important to remember that a top 10 name isn't what it used to be. Overall, there is more variation in names being used, so the top names make up a smaller percentage of babies being born.
Jack is short, so I could using both first and middle as a viable option if he wants to avoid being Jack S. But yes, Jack S. does sound like jack@ss. Though, I would imagine (hope) most teachers would recognize this and try to avoid Jack S in favor of Jack Full-last-name, especially if your last name isn't particularly complicated or difficult to pronounce.
I agree with your perception of Luke as a name that happens to be in the Bible, but isn't paritcularly Biblical in the same way as Noah. I don't think Luke would strike me as particularly religious unless it was paired with other Biblical names.
I like Kira quite a bit. I'm really not a fan of either McKenna or Linley.
My first thought was Charisma. Though, Charisma & Christa seem too close and Charisma is a bit more daring than her other choices. Is she a Buffy fan by any chance? I suppose the character name Cordelia could also be an option, assuming she is a Buffy fan.
Caprice also seems possible, as does Capri. Constance? But that doesn't strike me as very Hollywood. Coco? Again, that doesn't strike me as quite her style.
Do you think she'd do a reverse Khardashian and spell a K name with a C? Cayla? Cim? LOL
I'm not reallly a fan, but I don't think Jaina/Jayna is too far "out there" for it to be really problematic. It stikes me as a bit of a mash-up between the modern Jayda and more classic Jane. Because of the similarity to Jayda, I suspect you wouldn't have a lot of problems spelling it Jayna. Jaina strikes me as the spellling most likley to have problems.
Sorry, I'm just not a fan of Zephyrine.
I'd worry that Sappho could be problematic/lead to teasing.
I like Iphigenia, but I might worry about spelling/pronounciation issues. I suppose the nickname Genny could be an option if she wanted something to blend in more.
Apolline is nice.
Romane/Romaine is going to be lettuce for most people in the U.S. (assuming that's where you are).
I'm just not a fan of Vespertine.
Julia/Juliet/Juliana are lovely, but they seem a bit bland compared to your other names. These would certainly be a safe choice, but I get the feeling you aren't looking for a safe choice.
Angelou is nice.
My favorites are probably Pamina, Cosima, Heliodora & Philomena. However, I agree that Philomena is too similar to Philippina's name.
Theodora, Theodosia, Cordelia, Aurelia, Lucretia, Athanasia, Konstantina & Zenovia
I wouldn't use Charlotte or Caroline because of the repeated first initials. Charlotte is also way more popular than I think you want.
Phoebe is nice. But with sisters Chloe and Hannah, I do notice that Chloe & Phoebe seem to go together perhaps too well, making Hannah stand out a bit.
Juliet is my favorite. No shared initials and it fits well with both Chloe and Hannah.
My favorites on their own are Hugo Justice & Helena Joy.
But, I don't like matching initials for twins. So, I would probably do something like Simon Loyal & Helena Joy or Hugo Justice & Rose Amity.
Philippa/Pippa seems like a perfect fit with Georgiana/Georgie. I like how both given names are feminized versions of masculine names. However, the nickname Georgie is boyish, while Pippa is only ever used on girls. It seems to give you everything you like, but without boxing you into the corner of feminized name/boyish nickname for both. I would not use just Pippa, she may want more options later. Since Georgie has options, I think it'd be best to make sure her sister does too.
Louisa is nice, and I think it fits really well with Georgiana. I would also be concerned about Lou as a nickname, especially since it starts to set up the obvious theme you want to avoid. Perhaps Eloise? That could potentially lead to the nickname Elle/Ellie, though that's much more popular. I'll also suggest Lucinda/Lucille with the nickname Lucy. I really like the idea of Georgie and Lucy together and Lucinda/Lucille both seem like good style fits for Georgiana.
Frances is nice, but I would worry about Frankie as a possible nickname. Though, you could always insist on Fran or Franny, at least while she's too young to have a say!
Elizabeth/Betty is fantastic! It works just as well as Philippa/Pippa, just without the feminized masculine name. It does strike me as a bit less themey (though the theme with Philippa/Pippa isn't too much). I would vote for using the full Elizabeth instead of just Betty. Again, she may appreciate having more options when she gets older.
Beatrix is nice, would you use Bea as a nickname? I find I'm not quite as excited about it as Philippa or Elizabeth. I also noticed the nicknames Georgie and Bea are a bit rhymey.
Juniper is a suprising choice with the rest of your names, but it works. I think it's a very good option if you want a more eclectic sibling set. Georgie & Junie are also really cute together. I think Juniper rounds out my top 3 for you.
Bellamy feels all wrong. It strikes me as very much an outlier compared to your other name style. Juniper is a different feel, but it has June/Junie which makes it work with the more classic/traditional style of Georgiana. Bellamy strikes me as very modern/surname/trendy-and it just feels off next to all of your other names.
If the Paltrow association bothers you and you don't like Gwendolyn as much, perhaps Guinivere? It's perhaps a more daring choice, but it's always been my favorite of all the "Gwen" names.
I agree it would be helpful to have a better idea of what names you like, even if you can't use them.
Based only on Adam & Lucas, I'll suggest Noah, Abram, Marcus, Matthew, Matteo, Aaron, Evan, Joshua, Ian, Samuel & Jude.
I do like Maria Teresa, despite the fact it made me think of the historical figure. I think one good thing about the Empress is that she's just familiar enough that Maria Teresa just sound right together. I suspect a lot of people will think this, perhaps without realizing exactly why.
I also really, really like Flora Teresa or Flora Maria for you. I've a soft spot for Flora anyway, so it is by far my favorite from your list.
Yes, I didn't catch it right away. But after I saw Nina and Maria typed out next to each other, I also thought of the Nina, the Pinta and the Santa Maria. Not sure if it is enough to not use Maria, but I suspect you might get the occassional comment from someone trying to be funny. I suppose it depends on how much this would annoy the OP.
Serafina Kate is beautiful! I'm so glad you finally decide and I'm even happier that you are happy with the decision! I look forward to seeing you around the forums in the future. But right now, enjoy spending some time with little Serafina.
Helena, Flora & Vera would all work really well in English. They also strike just the right balance of familiar and fitting in, without being overly popular.
Since you want something that is on the less common side, I would avoid Eva, Isabel & Elisa. Eva/Ava and Isabel are very popular at the moment & Elisa has the potential get lost in a sea of other "el" names (though I don't think it's quite as problematic as Isabel & Eva).
I'm uncertain about Margarida. I like it, and I like that it could potentially have all of the Margaret nicknames. It does remind me a bit of Margarita, which most Americans will likely think of being an alcoholic drink more than "girl's name."
Maria & Tereza I'm also torn about. Familiar and not very common on today's kids, but they could strike some people as being "mom names."
Fernanda has just never been a name I cared for (I also don't like Fernando, Ferdinand, etc).