1.If you really feel you need to carry in WI, here are a few points to consider, as others above have posted.
Only YOU can make this decision, IANAL, and there are no guarantees. If you are caught with illegal CCW, you could get off Scot-free, or have the book thrown at you.
Wisconsin's (anti) CCW statute is "only" a misdemeanor penalty.
Many (but not all) of Wisconsin's DA's are loathe to touch CCW cases right now, for fear of sending more precedent cases to the Wisconsin Supreme Court.
The next ruling on the current Supreme Court case may well push WI into an "affirmative defense" state, where basically, if you're committing no crime, you can be arrested, but will likely get off in court if your carry was for a "lawful purpose".
Other alternatives:
OC Pepper spray is legal in WI. Fox Labs is an excellent brand. I recommend getting the inert practice canister along with the spray.
IIRC Wisconsin does not have a length limit listed in it's "knife law". I recommend keeping it visible with an external clip or belt pouch. "Switchblades" are illegal. However, a lockback knife that's not a "switchblade", but can be flicked open with a wrist-snap or arm-swing is illegal just like a switch blade. If you carry a folding knife that has an adjustable axis screw, keep it tight enough that it can't be flicked open.
Wisconsin - 941.24. Possession of switchblade knife. (1) Whoever manufactures, sells or offers to sell, transports, purchases, possesses or goes armed with any knife having a blade which opens by pressing a button, spring or other device in the handle or by gravity or by a thrust or movement is guilty of a Class A misdemeanor...
The Leatherman Surge has a rather large blade, and it can be accessed externally and opened one-handed with your thumb like any other lockback without unfolding the pliers. The fact that it's a multi-tool gives it a more "PC" factor if you encounter LEO's or bliss-ninny's.
Clubs and ASP/Monadnock collapsible batons are also illegal under WI 941.XX. However, if you're out walking the dog at night etc., an openly carried 4 or 6 cell Mag flashlight is not illegal. At least until you used it as a club, and then presumably actions were taken that you'd better be justified.
Other than the lack of CCW, WI is a pretty decent self-defense state. And barring massive failure at the polls this fall, I am confident we will get CCW eventually.
IIRC we do have self-defense lawsuit preemption. We are a "duty to retreat" state, but it's limited by the "reasonable person" modifier. Essentially, you've got a duty to retreat only if a "reasonable person"
feels they can safely do so. If you
feel you can't retreat safely, the duty to retreat evaporates. (IMO this is not too bothersome. All legality aside, fleeing, if practical, is what you
should do from a tactical standpoint, even if you are in a "Castle Doctrine" or "Make My Day" state…)
So in WI, being surrounded, outnumbered, fear turning your back on your attacker, not have the time to flee, be cornered, or have children or other household members with you that you can't grab etc. would all qualify. And you don't have to wait to be in that situation, you can reasonably
feel you were going to be forced into that situation too.
My take on the WI duty to retreat law is that it's there to snare the hothead who was in reality "spoiling for a fight" and had ample opportunity to leave, but claims self-defense. There's almost a million and one "reasonable" defenses that can be used. "I
felt he'd catch me if I ran." "I had my children/dog/Mother-in-law with me." "My back door was locked." "He was between me and my car." etc. etc. etc. And that's if you actually went to trial, which would be rare. Even if some of our big city DA's are despicably soft on crime none seem interested in malicious prosecution of self-defense cases.
I would love it if we were a "Castle Doctrine" or "No duty to retreat/Make My Day" state, but what we have isn't too bad. Prosecutorialy, you (almost) never hear about people getting rail-roaded for self-defense in WI.