Some properties have casitas (or a mother-in-law suite, etc.)

You'll be added as a party to the foreclosure suit as you have an interest in the property, but as you haven't signed the mortgage you won't be personally liable for the amount due.

I have been playing around with pricelabs, and am working on some pricing rule-sets that are best suited for the combo listing properties.

Exploit these advantages and find another opportunity that will suit the needs of your colleagues.Also, not sure what your rents and expenses look like on your current property with the 7 offices. 

I also run 3 longterm AirBNBs (1month - 6 month) at my primary residence (in-law suite) and we are fairly specific about the type of clientele (A and above, typically millennial) we allow into our house, which that screening rolls over to our rentals.

If you don’t like the Midwest then look for somewhere that suits you better. 

Does anyone have any recommendations on which loan would be best suited for the short term?

So there is such a variability in what data is available it's very hard to extract any meaningful data.I am not aware of any other online sources better suited, however.

This will also encourage them to find another place better suited. 

Now if he gives proper 60 day notice to leave on March 31, and you try to hold him to that April rent, then you are wandering in a grey area.