Not to sound too woo-woo, but for me, playing upright is as much about feel as it is about specific timbre. I don't play the same on bass guitar and some songs just "feel" better on upright. Plus sometimes it's about the bow. If a mag pickup gets me in the mix without a headache, I don't think I'm going to be bothered that It's not the "right", or the same timbre of my bass acoustically. Not to mention, when I hear recordings of NHOP playing with a mag pickup, there's still no mistaking it for anything other than an upright.
I don't know why I didn't think of this earlier, but there's a PA in my workshop and one of my shopmates did his studies in sound recording. I'm going to bring my bass in and see if he can give me a crash course in EQing and see how loud we can get the sucker. I know the room changes everything, but it's a start.