You know what was wrong with the Thieves Guild in Oblivion? They were a bunch of somber, bleeding hearts that were depressing as all get out. The dark brotherhood was more cheerful!
When I picture a medieval fantasy thief, I think of a devil-may-care rogue, suave and confident. The Thieves guild should actually sound excited when planning a heist!
And if the Thieves Guild in Oblivion really wanted to help the beggers, they'd steal them swords and say hey, there's kind of hundreds of dungeons you guys could loot, sell the stuff at the stores, and actually feed yourselves! Yes yes, it's dangerous, but definitely better than starving to death, better for their self-esteem than begging, and there's so many of them they could practically zerg the dungeons lol.
After all, if you give a man a fish, you feed him for a day. If you give him a sword to kill goblins to get their stuff to sell their stuff to buy fish, you feed him for a lifetime