The desired outcome is to turn-around some of the neighborhoods that have been on a steady decline for years.

Would like to optimize income stream in order to make steady upgrades to property.  

Part of the impetus for this idea was something I heard on our local NPR station about the city incentivizing development because our population growth is far outpacing our supply.

Supplying tenants with appropriate resources for money, food and other assistance. 

The challenge is supply-Where there use to be more supply than on average compared to the rest of Chicago, now there's less supply.

This includes mileage, phone, office supplies, etc.  

It seems as if home prices are inflated due to short term low supply.

He knew what pockets of Houston were hot sellers, what pockets had a lot of buildup and better to avoid, which areas had more competition, which areas had more equity, which areas had new home supply scheduled to come in.  

If you have 60 units, you can literally create your own market within your complex, and find your own supply/demand curve.  

Also to your point of the day care and company car, I think that's valid and I would add that it it might also look legally like a home office - she still maintains part of the house for her personal use (to store cleaning supplies and linens)., Interestingly enough my mother's best friend runs a day care out of her personal apartment in NYC.