We have a big place so it is families and groups.I do ask guests before booking if they are celebrating any special occasions and I will add some extra things to the welcome box that fits if I can.

I own one half, 3 bed 3 bath, and I’m currently living in and renovating it with plans to rent down the line.

Looks like an extra 2 months to get money in at 10% instead of 7%.  

The law does NOT apply to landlords:With less then 5 rental unitsThat live in one unit of a duplex and rent out the other unitThat rent out rooms in the home they occupySo, landlords can no longer state in their rental ads, "Section 8 not accepted".The reverse is also true, "Section 8 only", cannot be used.We've always recommended screening S8 tenants the same way as cash-paying tenants.Landlords waiving application fees and/or security deposits only for S8 prospects may also be violating Fair Housing.

I live in Sheboygan Falls, WI. 

Convince yourself that there's a better than average chance that you will lose, and if you can live with the time, energy and money spent if you do. 

Or paying off my debt, while I provide them with a nice house to live in instead of an apartment. 

I would start close to where you live personally. 

I used to live downtown and was on the zoning board.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!