Turn fence into "billboard" on private property?

I have a SFH on busy highway 51 in northern Wisconsin. It has a wooden “shadowbox” fence facing the highway that can be seen nearly a mile away. Every time I drive past I keep thinking that this fence could possibly make me money.

Can I turn this fence into a “billboard”? Was thinking allowing local businesses to put up vinyl signs, but want to be sure I’ll be legal in doing this. I called the town clerk regarding putting up a sign and was told they have a “sign ordinance”, but I’m not sure if that applies to billboards; didn’t ask for clarification.

Who should I contact to make sure I’m legal or is this something I shouldn’t even bother with? Has this ever been done?

To verify legality, you would need to file for a permit with the city. My bet is that it is not legal, unless your property is zoned commercial (sometimes you can be zoned commercial and still have a residential use). If it is illegal, then the odds are that if you put it up, other billboard companies would turn you in and you would be stopped by the city. The only exception would be a political message that you could claim was free speech – but even that argument does not always work.