Are you expecting full building penetration or something? Using a directional antenna at a window and a inside dwelling repeater I would say should be standard procedure. Full building penetration would mean every lightpole or every other lightpole must have an AP. I am going to assume thats what your talking about. Or is there extreme wifi interference (# of APs) that makes its impossible to use even with LOS to the AP? If you can't get a connection with LOS to the AP on the pole, your story is too fishy.
IEEE needs to be put in the stocks for not having transmit power control in WiFi (using minimum amount of power needed to reach client), because they have polluted 2.4ghz so badly in urban/suburban areas.