I think they are all pretty good. My reasoning for selecting the Privateers is that it is something I associate more with Halifax history, if this is supposed to be a Halifax team. Plus, I kinda like the skull and crossed swords logo.
The Highlanders logo and uniform looks pretty good, but I tend to associate that more with Cape Breton and the Scottish heritage therein. If it's supposed to be more of a Nova Scotia oriented team, then it's alright but change the name to Nova Scotia Highlanders because Halifax Highlanders seems kind of strange to me. The Citadel is about as 'highlands' as Halifax gets - or maybe Cowie Hill...