If you  do plan on moving into the quad you should identify what unit you desire - maybe based on the rent amount or the tenant behaviors, etc.. 

Pick your plan, look into the Kansas City area, use market comparisons, check your money power, look into loan options, put together a team, check cash flow, ROI, and Cap Rate, and make your bid after careful checks and talks.

Of course nothing goes exactly as planned; in one such deal the borrower was having trouble making payments and had an offer to sell which required me to carry back a second mortgage.  

But I would advise you have a plan in place to pay off the existing mortgage in 2-3 years because eventually the original seller will become unhappy with having a loan in their name and no house to show for it.Finally, there's a lot of irrational fear out there about the due on sale clause and the lender calling the note.

The first floor is a commercial space housing a pizza shop that grosses $800k annually.

All new Samsung appliances, new flooring, quartz and marble countertops throughout the unit, including all new wood and soft close cabinets and your own private fenced in yard great for entertaining and more.

I'm trying to figure out what kind of insurance plan to get that would be suitable for both these exit strategies. 

What kind of investments were you planning on focusing on?

I am going in with my eyes open and we shall see - I am a cynic like you, but plan for the worst is my way of viewing the investments

I will plan to reach out to in the future to better connect.