There's a bug with the "Old Guns" quest.

On my first play through i couldn't get past the dialogue between my character and Ronnie shaw, the game would just hang on the dialogue box,

Tried going back to earlier saves and still had the same issue.

Made a new character, got stuck again on the same quest, only this time i was able to get past the dialogue section and was able to complete the quest, however after this the radio station that i had to power up in order to call in artillery support went offline, no matter how many generators i setup (i tried as many as 10 large generators) the NPC manning the station says "We need to power up the transmitter so i can get back to broadcasting".

Seems to be a few issues with this particular quest.

Same issue on Xbox One. Doesn't matter how many generators are running and connected. The NPC just acts as if the transmitter isn't getting power and won't man his station.

It's pretty game-breaking and it's across all platforms, yet I don't see it addressed in the mega-issues thread. Maybe Bethesda guys haven't seen these posts? The issue is definitely out there for a sizable chunk of folks (those who did the optional part of tuning into the station during the old guns quest, anyway). There's a couple threads on reddit with complaints and the answer was to just revert to an old save.

Can we get this on the list of things to look into? I didn't notice it was broken until five+ hours in and going back to an old save... meh. I'll just live without whatever quests\updates the radio tower would have given me and hope for a patch.

I keep getting stuck with the Ronnie Shaw not recognizing that I have setup the guns. or placed them in position. But keeps telling me to set up the guns.

yep its a bug just took the quest to the point where I am supposed to throw a flare and moved on...with so many bugs and glitches it may never get done.

Could be a bug, although where have you put the guns? I put them on the wall corners / in the circular area - just 2 on top, and 2 in the walls. Then I think you have to assign at least 1 settler to the gun. That should work.
Also, to the North of the castle, just outside in the water, there's a huge water filter. Store it on the workshop & you wont have to build a new one. I placed it on the other side, opposite, near the broken wall in the water. I needed to run new lines to it, but it works a treat.

Bugs svck. If it's broken for you, damn. Keep trying though.