It sure would be nice if the webstream audio was offered in high quality high bandwidth stereo. I could be wrong, but the trend seems to be that most of your listeners will eventually only be listening to their smartphones, computer speakers, and in car on-line listening. Why not provide them with a high quality signal?
I also hope that's in the works. I'm sure the current stream is a holdover from the previous format, which was mostly talk. Right now, it basically sounds like AM radio.
They do plan on moving the station from the current Capitol Drive studios out to the new MRA complex in Menomonee Falls eventually. Perhaps with the (likely) new equipment, 1290 will be upgraded a bit, including a better webstream (hey, Clear Channel can make AMs sound like FMs on IHeart, so why not them?). I also think they should put the station on an HD2 of one of their FMs (like B93). It would probably solve the current problem they have of not being able to provide an online playlist due to being on AM.