You seem like a really decent, sincere person, and that's why I'm writing in response to your request for suggestions / ideas about your proposed circumnavigation of Lake Michigan.
Earlier this year, another decent and sincere paddler, someone with a good deal more kayaking experience than you, drowned on Lake Superior while attempting a solo circumnavigation to raise money for a good cause. Here's one account of the tragedy: http://www.canoekayak.com/touring-kayak/loss-on-lake-superior/.
What you're proposing - a late-season, solo circumnavigation of Lake Michigan - is a similar undertaking; one that will very likely turn out to be the last trip you ever take. As things stand on the eve of your departure, you have almost no chance of surviving the attempt.
The biggest problem you face is that you don't have the experience or knowledge about open-water kayaking to appreciate just how dangerous your proposed trip will be. Michigan is huge lake, with lethally cold water, guaranteed bad weather, high winds, big waves, and very rough conditions that you are not, by any stretch of the imagination, prepared to encounter. I don't mean that as a personal criticism; it's just the reality that you're up against: you're proposing to pit your limited skills and experience against very dangerous conditions in an unforgiving environment where you have zero margin for error. In other words: One mistake = you die.
On your web site, you mention your serious injury and a recovery that's still in progress:
"a complicated tibia break in two places and a complex series of fractures in my ankle which to date have left me with a limp, severe pain, and an unknown window of recovery".
Your proposed trip would be tough enough if you were traveling as one of a group of expert paddlers. But you're not an expert paddler, and you're going solo, in rough weather, with a bad injury from which you have yet to recover.
You also point out that you essentially have no plan for the expedition:
"The Plan: This is the best part. I don't have one. I don't overthink things, its a big lake with a fair number of cities of towns along the way (Chicago and Milwaukee to name a few). I will leave with approximately one weeks food rations, and minimal equiment, a tent and clothing - I'll figure the rest out along the way."
You make that statement as if being unprepared for a very dangerous undertaking was a virtue. It's not. It's a clear indication that you don't give nature the respect that it deserves. In my 40+ years of outdoor experience, that's the most dangerous attitude that anyone can take into the great outdoors.
You're a climber, not a paddler, so as a fellow climber, let me try and put all this in perspective: what you're proposing is like a 5.7 climber, with no cold-weather experience, announcing that he's going to attempt the solo, off-season climb of a heavily glaciated, high altitude mountain. It doesn't make any difference how many towns or cities are nearby; if you're by yourself, lying at the bottom of a crevasse with a broken leg, you're as good as dead.
Mat, I sincerely hope that you'll reconsider your decision to attempt the circumnavigation this year. Give your injuries time to heal, get a lot more open-water kayaking experience, learn about the lethal nature of cold water, get the right gear, plan meticulously, and then do the trip with at least one experienced mate. I'm not overly optimistic that what I've written here will change your mind, but since you placed your request on this forum, I felt obligated to try.