I don't like mixing the two - it can get messy if he stops mowing due to mechanical or health issues, etc.

So are there reports that I can ask which can tell me the financial health of the company?

I'll take having a health care directive over 10 LLC's any day.  

I currently enjoy my full time job in health care, but would love to cut down on my hours in another 5-10 years.

You could lease part for food service or coffee shop and some retail space, a small health club, massage. 

For the most part its just health and safety items, which are items we should have remedied anyways.As someone else mentioned, biggest thing to avoid is having the house tagged as vacant which the city will do if it sits empty for too long (handful of months, grass not cut, etc).

On the one hand, I can see it as a positive indicator, for example of market health and increasing suburbanization. 

Last month Atrium Health purchased 40 acres a mile down the road. 

But I draw the line when there is risk of damage to the property, annoyance to the neighbors, health concerns, pests, etc.

And in many cases this may be warranted as health and safety issues may be present.