I saw on a website that wearing the Silver Shroud costume gave some amusing dialog. Is this just in one spot or throughout?
I have found that the costume is not adequate to my defensive needs. I have it on now but am wearing power armor over it.

1) Does it trigger these options if I am in the Shroud costume in power armor?

2) Are the conversation options throughout or just in one spot? IE can I wear my power armor then just switch when I get to a particular npc?

I think you just need it for the final battle with the Mechanist. Which was a real pain, I had to turn the difficulty down because all the explosions kept killing me.

http://imgur.com/a/SZmEH

Yeah, before the DLC I was walking through things so I cranked the difficulty up and everything was fine. WHen the DLC came out I went into the first building they told me to go to saw a Legendary robot with what I think was a gattling laser who killed me in 3 seconds. I was forced to grab my seldom used Power Armor.

needed for the final battle like said, suggestion bring a lot of mines and set them while the mechanist monologs. if set right only have to deal with eye bots and swarmers.

Do you still get those options if you are not the Shroud? I haven't even been to Good Neighbor yet and have no plans to.

I have no idea. I went and talked to the guy just to be safe before I went in.

I wore my shroud costume at first and used the Shroud dialog options, but when I saw a Persuasion challenge option, I panned away, accessed inventory and put on a +2 CHA outfit and popped a Graqe Mentat, so none of the subsequent dialog options had a Shroud option at all. That said, the Mechanist's dialog does not appear to differ very much at all (if at all).

Well I didn't care that much about the Shroud dialog, but I did want those dialog options near the end there.