Since it has been suggested that Neal took on some of Rumple’s traits this season (eg, using Roland as bait to get to Henry)
I would be incredibly surprised if that happened. Neal has always been appalled by the way his father would harm and/or kill people. The thing with Roland was a carefully considered plan, with safety measures in place to ensure no harm befell the kid. If there had been a risk of the Shadow going back for Roland later, I daresay we’d have seen it by now, considering they’ve just captured the Shadow. So whatever people wanna speculate about Neal’s actions with that, as far as canon goes, it’s looking pretty likely that his plan didn’t result in any harm to Roland.
Also, turns out the shadow isn’t THAT scary if it can be captured in a coconut with a candle. I mean, that’s all we needed to rid ourselves of the big scary shadow? Terrifying! 303 made the shadow appear much more horrifying that it actually turned out to be. And like Phee said, it was carefully planned out. Mulan was there in her infinite awesomeness. As was RH and Little John. And literally the next scene at the Dark One’s castle is Roland sleeping peacefully under the same window, RH telling Mulan that everything is perfectly fine and that there wasn’t a scratch on him.
Do you know what that scene in 303 DID show? That Henry comes first to Neal. His family comes first in his mind and heart. All he has is his boy and the idea of a second chance with Emma. Of the two men, so far, Neal is the only one who’s interest aligns with Emma.
I think the only thing that would make Neal even consider harming Hook, would be if Hook harmed Emma.
He wouldn’t even hurt the Lost Boys! He flat out tells Rumple in 304, “no killing the lost boys”