Are you still based at Hammond? Just starting a similar search for liveaboard near Chicago!
I lived aboard for a few years in various Great Lakes ports. My advice would be to pull the boat right before the freeze and live on the hard. Bubblers and stuff are great but with a lengthy cold snap they can be rendered useless. Not to mention if heat fails while you're at work you can obviously have problems. At a minus -10 degrees you'll have about an hour before water lines start bursting. I know from experience.
Marinas won't have a policy for living on stilts (or for allowing it) but if you charm a marina manager he/she will likely let it happen.
I'd winterize the boat. Shrink wrap it. And hang weighted tarps from the toe rails to minimize wind sheer against the hull. Makes it much easier to heat. Have your drinking water and stuff aboard but shower in the marina building. One year I got a YMCA membership just so I could shower and I ended up losing pounds since I started working out and swimming. Not bad for a few bucks a month.
Around Chicago there are lots of commercial yards that just might entertain your prospects. But if it's anywhere near where there is tug traffic you'll get crushed. Areas that haven't froze in 25 years got sealed over this year. Any commercial boats running in ice will have no concern for The plastic boat over in the corner. Ice compression is a concern.
Anyway, hope that helps.