Some work swing shift, some day shift, some are retired etc etc.  

The caregivers don't live there, they just work on shifts.

Legally speaking there has to be a duty and I don't think the doctor has a duty to every single person in society who the dog might come in contact with.

Now to shift to income generation and additional  savings for next year provided I survive being a landlord

When supply outpaces demand and market conditions shift that is when you can be left treading water for years mid project waiting for the next up cycle or if you can't hold on let it go and lose big.

So you cant find homes that are damaged and distressed but you can find homes that are just really outdated and ugly.If you cant find a good multi family then maybe you should shift gears and focus on finding a home you can convert into a multi-family.  

My personal risk tolerance would shift me far away from that area.

This is true even considering the population shift in Chicago in the last 2-3 years.I think overall, I think hotels still have the stronghold in the corporate market - I do know that there is a huge pull for Millennials to travel using Airbnb, particularly for leisure.

If you are trying to shift liability for work being done around the property, then yes.

Since the turn over rate of new LT's coming to flight school is so high (most only stay 18 months) the pockets of successful developments shifts rapidly.