Not sure how it works in Milwaukee but here in Chicago we’ve made progress by working with city council members, electing mayors/alders that care about the issue, building a strong biking community, and trying to engage CDOT. I recommend figuring out your local city council person and try to get them to help you as the first step. If it’s not already happening you might want to try to organize critical mass. I’d love to Amtrak up to Milwaukee and bike to my favorite places and friends that live there.
We do have a local Critical Mass ride! https://www.mkecriticalmass.com/
Awesome. You can use this to meet like minded people and build each other up. The more people asking for things the harder it will be for your local government to ignore you. We have little sub groups / organizations that have come up over time like bike grid now as well that has really active in driving engagement and lobbying for a specific plan at public meetings. Feel free to ask more questions, I live in a bike unfriendly part of Chicago and have been working through this for the past several years and currently working with the city to have us included and holding them accountable for following through.
IIRC, the city allocated a measly $500,000 protected bike lane fund, which is at least greater than $0, but I’m not sure if any projects have used that money yet this year. I believe part of Hawley Road also had barriers like that installed, but I don’t remember how recently.