@Dan Brewer as I'm sure you're well aware, people aren't in this because they don't understand it.

How did you finance this deal?

@Kim Huard I am a real estate broker and investor in Oxford, so I can share some first hand experience with this market.

Did you do this deal or was it one of your clients? 

You would want it to appraise for $200k (assuming they require 20% down + closing costs) so you would then have a $200k loan but have received your $150k back to do it all again. you could also do this with a bridge fix and flip loan as well.

This is both a legal and tax question. 

I have personally house hacked for over 10 years and continue to do it to this day, right here is St.

If you can help with the terms of the mortgage I could better assess how I would work on this deal.Have you considered lease option in it's current state?

In the past, tenants at this location have always used it as is, without modification.

Also, we filed a claim this year due to the hail storm in South Milwaukee so our roof was covered in that.