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I don't think you can go wrong with any of these names! I would pick Miles or Oliver, but really all of them are great.

Boy: Gregory Charles
Girl: Matilda Jo

Maternal grandmother was Patricia went by Pat
Paternal grandmother was Ann

I plan to use Ann or some variant of it for one of my future daughter

I love Ronan for you. It means little seal. Griffin, Corbin, and Ronan

I like Libby. Hate Beth and Liz/Lizzie.

You can't go wrong with either. I do agree with pp about the double I's of Isaac and Ian. That's totally a personal preference thing tho.

Louise Winslow "LouLou"
Matilda Josephine "MJ"
Hazel Genevieve
Ruth Helen "Ruthie"
Zoe Ann
Theodora Riley "Thora"
Agnes Lee "Aggie"
Sylvia Heather
Katherine Patricia "Katie"
Nora Lin

A family comes into my work alot. They have two kids Oliver and Dorothy. They go by Olly and Dot.

Harold (nn Harry) and Edgar (nn Eddie)

I'm the exact same way! It's either none the same or all the same. Other than that I would say the style doesn't so much matter to me, but they have to sound good together. For example, right now I...

From your list I like Niamh and Keira. My cousin is Niamh, and yes she gets spelling issues a LOT, but she loves her name anyway. Pronunciation is only an issue when someone reads her name first,...

In Boston, MA I'm always seeing lots of classics. John, James, Micheal, Mary, Catherine, Caroline (I personally know at least 2 of each under 8).

I love Agatha, but only with the nickname Aggie. Hattie seems way off to me.

I love the name Helena, and pronounce it the way you do. I worry that it would lead to correcting people her whole life, but I don't think it's a deal breaker. I would still use it, and spell it the...

Grandparents:
Ann (no middle)
David (don't know his middle)
Henry Joseph
Patricia (don't know middle)
James Cornelius

Great Grandparents:
Helen Winthrop
Norman (don't know middle, but fun...

I think that boys names ending in -en, -in, or -on could work with your last name just fine, but I would stay away from -sen or -son endings.

Girls:
Matilda, nn Tilly or Tilda (middle name...

It's funny, I've always loved names, but never paid much thought to my own! It (Amy) always seemed kind of boring to me, and I kind of thought it was seemed too "grown up" to me. I was born in 1990,...

Speaking as someone who was given a name that was very, very popular (#2) a good 20 year before I was born, I would say it is really not that big of a deal. Yeah in middle school I sometimes wished...

I just met an Aviva (pronounced uh-vee-vah). It's Hebrew.

Tabitha and Matilda? They've been in my top 5 girls names for a long time, and I only just noticed that they have very similar structures (they share all of the same vowels, amount of letters, etc)....

Oh, I'd also like to second ash's suggestion of Sebastian Eli Morgado. That way you get to use both of your favorite names! It sounds great together.

Sebastian is the same amount of syllables as Caroline. It's more letters, but so what? I would pair it with a shorted middle name if it's that big of a deal to you.

I also like Eli, and have...

I don't think BJ is a big deal. Went to high school with a kid who went by those initials, and by the time anyone in our grade realized the humor in it, it was more in a "haha that's cool" kind of a...

Romy and Mo are cute

I went to high school with a girl who was named after her mother, they were both Carol Ann lastname and the daughter went by Carol Ann.

I think that while it is a bit unusual, it's only fair that...