[name_m]Ike[/name_m] – I like it well enough, I certainly can see the clunky-retro appeal. It has a somewhat abrupt sound though. I do like it with your older boys, but again, there are a few similarities with [name_m]Clyde[/name_m] with the long ‘i’, hard ‘k’ sound and one syllable. [name_m]Ike[/name_m] [name_m]Augustine[/name_m] is a cool balance of style but I actually prefer [name_m]Ike[/name_m] [name_m]Benjamin[/name_m] as a combination. [name_m]The[/name_m] 'k’and ‘g’ in [name_m]Ike[/name_m] [name_m]Augustine[/name_m] feel a bit awkward so close together.
[name_m]Dwight[/name_m] – I’m not convinced on [name_m]Dwight[/name_m]. I do immediately think of the character from [name_m]The[/name_m] Office who is generally well-liked. It’s massively popular though (probably has countless memes) and my husband rewatches it every few years. My next association would be [name_m]Dwight[/name_m] D. [name_m]Eisenhower[/name_m].
I agree it reads clunky-nerdy but it may also come across as a bit of a joke name as well. There’s [name_f]Dwayne[/name_f] and [name_m]Dwyer[/name_m] in the ‘Dw’ family but those have a different feel. I personally wouldn’t use it unless it had personal significance because the associations are so prominent.
[name_m]Gilmore[/name_m] – This is all surname to me. I’m not too keen on it. I do think of [name_m]Gilmore[/name_m] Girls (which I’m very slowly making my way through as a first time viewer). I didn’t think of [name_f]Happy[/name_f] [name_m]Gilmore[/name_m] but that doesn’t strike me as problematic. I’m also generally not a fan of using unestablished surnames as first names when there’s no personal significance.
If I may make a couple suggestions, these names made me think of:
[name_m]Delmer[/name_m] & [name_m]Delmore[/name_m] - Similar to Elmer/Gilmore
[name_m]Dennis[/name_m] - Mix of Delmer/Linus nickname [name_m]Denny[/name_m]?
[name_m]Gilligan[/name_m] & Gilan - [name_m]Gil[/name_m] alternatives
[name_m]Griffin[/name_m] - Seems like your style
[name_m]Grantley[/name_m] - Off-beat surname
[name_m]Edison[/name_m] – Nickname Ned/Sonny perhaps?