God I miss the Gray Fox.
Someone like him would have made the Skyrim thieves guild so much more than it is right now.
The guilds in Skyrim weren't as... Noticed outside of them as they were in Oblivion.
But it kind of makes sense...
In Oblivion, some portals opened up, mostly in the wilds, and the all the cities in Oblivion had walls and full guard-staff. There were always like 3 guards on each side of the gate, plus 5-15 patrollign the city, and there were always Imperial Legion mounted soldiers patrolling the roads. They were most likely less worried.
In Skyrim, there are dragons, a civil war and a lot more natural dangers that in Oblivion imo. Plus, only some cities are walled, and the guards are like 2 at each gate, 1-4 patrolling the city.