If I may, a lot of the issues we are running into with insurance is that consumers no longer use insurance as a catastrophic fall back but rather, they nickel and dime on small claims that compund into larger issues. 

Yes 1k sqft is small but probably much better than living with family.

Whether it’s advice, joint ventures, or even just sharing your experiences, your input would mean a lot.Feel free to drop a comment below or message me directly.

I was in national construction for 5+ years I'm not afraid of a small contractor who's ripping you guys off 

This reduces exit options and affects the value. 10) Small number of small units is the most expensive residential development there is.

As a SFR investor for over 15 years I have been wrestling with this question in the past, because it feels like you should upgrade to "bigger".I know for sure that I would not enjoy the ownership experience that comes with a small 4F, because in Milwaukee that typically also means lower income tenants. 

, 2) it manages the properties directly so there are many hands in the cookie jar, and 3) how/when/impact if "they" decide to liquidate properties and what would be the exact impact to me? 

If it is a direct lender you are able to work to find more favorable terms because they usually determine their terms on a deal by deal basis. 

There is a small (<600 sf) house on the lot currently, which is in pretty rough shape. 

We rarely have issues, but it seems like such a small investment in time and money to take one day to verify.