Yeah, so I wanted to talk to Mr. Holdout to do the Sneak Check 50 to get better hold out items. Now he says I'm too well known to discuss matters with him.

Great.

So, something that bypasses the need to talk to Mr. Holdout to get better holdout items once you reach 50 would be swell.

AFAIK you don't need to talk to him, it happens automatically.

Definitely true, I pack "Sneak 50" holdouts into casinos routinely and haven't spoken to Mr. Holdout at all.

Interesting

Same here. Only my first character has ever given him the time of day, and most of my (what am I on now... sixth?) characters have taken a holdout weapon at the very least into the Tops to deal with business in the suite upstairs.

(Other than the female character I had with Black Widow... *chuckle*)

Yeah, you don't need Mr. Holdout at all. It's the type of weapon that matters, not who you get it from. Here's a list: http://fallout.wikia.com/wiki/Holdout_weapons

I love the fact I can hide forty pounds of grenades, dynamite, C-4 and a detonator without any problem. And they'll let me take in a Power Fist, but always confiscate my Boxing Gloves.