The way they run the low modulation and narrow bandwidth for the IBOC on this station, I would doubt you will hear it in Milwaukee even after the upgrade.
From what I remember, the station is/was running IBOC and that required them to lower their analog modulation. I guess the concept was that they want their analog signal to have a similar "uncompressed" quality as the digital signal.
Univision was doing the same thing on WIND back in 2004 before it was sold to Salem....now WIND has the loudness that has become the norm on the AM band. The whole IBOC thing seems like a waste to me