New River does have weather guessers, but they're boobs. I've seen 500/1 broadcast on ATIS, only to be poking along at 65 knots and 75 feet trying to stay clear of clouds.
You got screwed. Sort of. If I remember correctly, they can't issue a flimsy number for a VFR flight plan if there is IMC/Convective SIGMETS enroute. Without a flimsy number, you can't file. That might have been what he was getting at.
As for the 53's/AH-1's taking off and flying - we don't need to file a flight plan, because we're covered by our flight schedule (as long as we remain in the local area), and they were just utilizing the VFR/Special VFR course rules in the area.
If it was me - I would have filed IFR (we're allowed to, because all our aircraft are IFR capable), then asked to depart Special V and canceled as soon as I was out of tower's airspace. Fuck 'em, it's not like Bragg is that far away. If you're interested, I think I still have the Special V course rules brief laying around somewhere and can shoot it to you. I've never flown into Bragg, but I flew into and out of New River for 4 years.