Just an update on this:
First, the law was created by a handful of retired guys that don’t know the first thing about caching. I know a few of the gentlemen. They are actually very nice and well meaning, but were clueless. I made sure to give them my two cents when I ran into them. They were afraid people were putting pornography and illegal items in the containers (obviously clueless). I informed them how this would mostly hurt their tourism, as most cachers just stop at a park or in an area on their way though to grab a quick cache.
Anyways, as I’ve been looking at placing my own cache, I viewed the Parks and Rec page to discover they are no longer requiring payment for the permit. They do however still require a permit to place a cache in any Jefferson County park. A slight pain, but at least you don’t have to pay. You can find more info here: http://www.jeffersoncountywi.gov/jc/public/jchome.php?page_id=1777