If the roomba detects a stall from wires it will reverse the brushes to free the jam. But it is best to run the wires along a wall or get them out of the way.
You should empty the bin (no need to clean it) and clean the brushes after each run initially. Once you get a feel for how full the bin gets and how dirty the brushes are you may be able to skip one or more cleanings.
Reds x 3, Dirt Dog, Disco (now a parts bot), Create, Scooba 350, and Security Dawg