Your friend is aware that the viaduct is coming down (at least that's the plan) and the the commute from WS to downtown is going to become not so easy, for a couple-three years right?
With that caveat, I think the idea of driving around the neighborhoods is a very good one. When we were looking for a place, we found a house near Graham and 48th for $1,400 a month, and more than a few houses down in Arbor Heights and Roxbury in that price range or even a little less. Now, that's not quite the Junction, but there are a lot of houses of all sizes and prices all up and down off California and Fauntleroy. I get the sense that many are advertised only by word of mouth or signs on the house.
You might also check with some of the agencies on California: Keller Williams manages some rental properties, and there are a couple of other agencies as well. Associates West is another, I think. Sorry, can't remember the names of them, but a Google search should get you some names. "Property Management 98136"