After a long list we seemed to have narrowed it down to 3, but very conflicted on them. Big sister is [name]Skyler[/name], and our last name is Irish, 3 syllables, starts with a G and ends in a Y.
My first choice is [name]Maxwell[/name] (I like it because my maiden name starts with an M and it ties in my Scottish heritage). I like [name]Max[/name] as a nickname but am concerned on how popular it is getting. Another name we like is [name]Gavin[/name]. [name]Even[/name] though our last name starts with a G, the alliteration doesn’t bother me and we think it actually works well. But I’m also concerned about how popular it’s getting, although I haven’t met any little Gavins yet. We would like something not too common but not too out there that people haven’t heard of it.
Husband really likes [name]Desmond[/name], which I am trying to like but it doesn’t feel right to me.
I’m indifferent on a middle name but husband really likes [name]Lee[/name] or [name]Leo[/name] to honor his grandmother (her name is Pasqualina but she goes by [name]Lena[/name] or [name]Lee[/name]). But the middle name [name]Lee[/name] would not go well with [name]Maxwell[/name]. 
Opinions and suggestions are greatly appreciated! We have 4 months to go so plenty of time. I’m just obsessing. 
[name]Maxwell[/name] is a nice name, as is the nickname [name]Max[/name]. However, it’s very popular, and a problem I’ve seen with the name is the nickname Maxxy, which could then lead to ‘maxi pad’ etc!
I personally don’t like [name]Gavin[/name] as I had a P.E. teacher named [name]Gavin[/name] and it’d be like I was naming my child after him! Although this is obviously your child, so it’s different for you 
[name]Desmond[/name] is terrible in my opinion! Very very middle-aged! I’d be a very embarrassed teenager if I had that name!
I think [name]Maxwell[/name] [name]Lee[/name] go together well Obviously depends on your surname though.
I like [name]Maxwell[/name], but it is very popular. Plus, it’s also a very popular name for dogs. A friend of mine has a [name]Max[/name] and he says that when they go to the dog park, his child gets very confused.
I think [name]Gavin[/name] is a very cute name. Popular, but not terribly so - well, I haven’t met any little [name]Gavin[/name]'s and my pregnant friends don’t seem interested in the name.
I actually like [name]Desmond[/name] as well. It sounds rugged and distinguished to me, but out of the three, [name]Gavin[/name] is my favorite. I think [name]Gavin[/name] [name]Lee[/name] is adorable.
Other suggestions:
[name]Miles[/name]
[name]Nathaniel[/name]
[name]Declan[/name]
[name]Graham[/name]
[name]Xavier[/name]
[name]Calvin[/name]
[name]Malcolm[/name]
[name]Ian[/name]
[name]Caleb[/name]
I like [name]Max[/name] Gy a lot, as well as [name]Maxwell[/name] Gy.
I’m fond of alliteration as well so [name]Gavin[/name] G******y rings beautifully for me as well.
I’m not sure which of the two I prefer. [name]Max[/name] has a stronger, surer sound. [name]Gavin[/name] feels more artistic and calm.
As much as I love [name]Leo[/name], I think I prefer [name]Lee[/name] for both since 2 syllables in each name always feel a bit clunky to me.
[name]Maxwell[/name] [name]Lee[/name]
[name]Gavin[/name] [name]Lee[/name]
[name]Desmond[/name]…hmm, I don’t hate it and [name]Des[/name] is kinda cool, but I like [name]Max[/name] and [name]Gavin[/name] better.
Thanks for the awesome responses!
I am actually more partial to [name]Maxwell[/name] than [name]Max[/name], probably because of the popularity factor (and my daughter is watching a lot of “[name]Max[/name] & [name]Ruby[/name]” lately so [name]Max[/name] is played out in my head). And I think [name]Skyler[/name] & [name]Maxwell[/name] make a great sibset. Although I assume the nn [name]Max[/name] would be inevitable. I also think [name]Maxwell[/name] [name]Lee[/name] sounds fine but husband seems to think you can’t have the middle name start with the same letter that the first ends with.
I do think [name]Gavin[/name] [name]Lee[/name] sounds pretty awesome as well but just not sure I’m “in love” w/ [name]Gavin[/name].
Thanks for the name suggestions, sadlola. Many of them have associations for either me or DH, but [name]Calvin[/name] & [name]Malcolm[/name] are good possibilities. I really like [name]Graham[/name] but our last name also has a silent H so visually it doesn’t look right. [name]Xavier[/name] is pretty awesome (I seem to be attracted to names with an “X”).