I’m currently visiting my family in Zenda, WI, a tiny town just south of Lake Geneva and on the border of Illinois.

You can find both on Facebook.  

I own some rentals in Cleveland and Milwaukee and I am a couple of weeks from closing on another multi family in Wisconsin.

If they don't then try to find a bank that will allow this work around.

I would love to help you find a duplex that meets your need to do a house hack!

So far no luck finding an insurer.

@Reitta Seidel, yes.Maybe sharing some of your thoughts that made you post this question will yield more valuable feedback.In my market, single family homes sell all year round.  

Hi there - I have a long term single family rental that will be sold in the next 60 days ($200,000) as it doesn't make me much monthly.  

Over time, the benefits of house hacking, including potential rent increases and the ability to live affordably while building equity, can far outweigh the initial concern over under-market rents.Keep your focus on the long-term gains, and you'll likely find that house hacking is one of the smartest financial moves you can make.

This is most important for anything that's a new renovation... if we find stuff on an inspection that a renovator should have caught, certainly knew about, and didn't fix correctly, it's an indicator that the entire renovation is suspect.