Soo.. i am now guild master and Listener in both guilds... but i still get some random encounters with assassins trying to kill me with a letter from astrid ( yeah she's dead )
and i run in some thieves from time to time also trying to kill me without the option to tell them im with the guild... kinda breaks the immersion, or whats left of it anyway.

Don't think you are supposed to get the assassins, but the thieves, yes, they are supposed to accost you after being Guild Master. IIIRC, if you are wearing Nightingale armor when a thief shows up, they won't demand money from you (but don't quote me on that). It's not immersion-breaking (on the thieves, that is) - thievery is actually supposed to go up. I know that the random night thief in the town of Riften seems to show up alot more the further you progress in the questline.

I'm not sure about the Nightingale armor. My TG character wears it most of the time, and I still get stopped by thieves - but she hasn't been wearing it ALL the time, so I might be wrong there. I only got the option to say I was in the Guild the first time, though. I just assume that the rest of the random thieves are working on their own

(And the random thief in Riften shows up EVERY night, I swear, even though I'm not Guild Master...)

I've been stopped by thieves whilst wearing Nightingale armour and they've given me money !!!!

I've never kept track of what my character was wearing when a thief showed up demanding money. I just assumed they were not with the guild and just random dummies for sword practice. The thieve's guild stresses no killing and these guys are more then willing to draw a blade when I say "I don't have time for this" and walk off.

I did notice something odd. doubt its a bug, more like poor programming. I am now the Listener for Brotherhood as well as returned thieves guild to its former glory and am its master. I stole a lot of potions from solitude and she sent the brotherhood after me. Whats funny is as the only Listener in Skyrim... shouldn't I have heard the contract about myself? This happened when I was doing the final quests for Nazem and when I returned to the brotherhood I had to pay him for my deeds against the brotherhood before he would let me continue with the quest he gave me. weird.

haha who knows.

Anyone who is hostile towards me dies... I don't care who they belong to.

Also agree. Stick 'em with the pointy end.

I kinda miss being attacked by DB assassins. It was so fun being attacked on sight by a group of imperials, stormcloaks, thalmors and a DB assassin at the same time.

That's impressive. My worst (best?) was bear + Boethiah cultist + thief + "random ice mage out of nowhere". It was pretty funny because the bear is hostile to everyone, and they just kind of got confused for a minute. I ran like the wind. Faendal caught up with me like an hour later. He acted normal but I could totally tell what he was thinking.

My best so far was when I was "escorting" Ulfric back to Windhelm after the Battle of Solitude.

One mammoth, two giants, three bandits, and two frostbite spiders. I'm not even sure who was fighting who, but everybody but us ended up dead. I couldn't even figure out how to get all the carnage in the frame.

http://img402.imageshack.us/img402/6964/stalk10.jpg

Sadly the Boethiah cultist was late to the party and didn't pop up until we were halfway through the Pale. Ulfric also waded all the way across the River Yorgrim to rain unholy destruction on a mudcrab that was looking at him funny. I think he might have PTSD or something.

The wilderness thieves are ostensibly Thieves Guild members; their intended behavior was that if they stopped you and you were wearing Thieves Guild armor, they'd say hello and give you some lockpicks, if you were wearing Nightingale armor they would give you money, and if you were carrying the armor but not wearing it, you could tell them about your status and they'd let you go.

The conditions on the dialogue are messed up, though -- they'll never give you lockpicks because it wants you to be wearing the unplayable NPC Thieves Guild armor, it only recognizes one of the three leveled Nightingale armor sets, and Guild Master's armor is not considered to exempt you from robbery. You can, however, simply carry a piece of Thieves Guild armor and they will let you go if you mention you're in the guild.

Wilderness assassins should cease when "With Friends Like These" is through.

Maybe he thought it looked like Elenwen.

Well, she always did look a little crabby.