I'm a Playbook neophyte, but I think it requires USB transfer, because that's how Developmental Mode is set up. Any idea why USB transfer doesn't work? Or is it just with BBH that it's not working for you? For me, I didn't have any luck with BBH, but had no problems with DDPB. If you need something to convert APK files to BAR files instead of expecting the program to do it, you can also use http://apk2bar.unker.net/.
My old PC just won't recognize it. Had to set up network sharing so I could actually transfer my music to the playbook. I tried googling the problem, but nobody seemed to have the same problem.