Which is better the Nightingale Black Armor or the Thieves Guild?
As Sam said, they are different. If you're planning on lots of breaking-and-entering activities, the Thieve's Guild armor is better. If you're planning on a lot of stalking and killing activities, the Nightengale armor is better. I have both; I wear the Nightengale armor for general adventuring, sometimes replacing the hood with http://elderscrolls.wikia.com/wiki/Krosis_%28Mask%29 when a particular quest or encounter justifies doing so. I wear the Thieve's Guild armor when a quest clearly requires lots of pickpocketing, lockpicking, and carrying off loot.
And regarding your original question, I returned the Skeleton Key. Picking locks isn't particularly difficult, and gaining skill at doing it is part of the intended game play.