From Wisconsin as well. After the intimidation and analysis paralysis of searching, reading, watching and listening to all of the good and bad information out there, I've determined that just going and trying something is the only real way to go about it.
I've accumulated points in a few states and am going on a DIY, solo hunt this September. Trying to plan around buddies and having "the best access, lowest pressure, best success rates" was driving me nuts trying to decide. All in ill be close to $5,000. That's including Tag/license, Food, Fuel (1/5th of the cost), gear needed that I didn't have (exo 4800, bino harness, camping gear).
Simply put, just gotta pick something and go for it.