I personally look for SFHs with separate living areas/kitchens/entrances.

Do you care if the community has amenities like pools, green belts, and gated entrances?  

 What about starting a new company and offering him entrance as an LP with some structure that offers less ownership but maybe preferred returns. 

Here is what I have for costs on a 22 unit building in Moncton:Insurance: $7500Cleaning (common areas, with 4 entrances, 3 stories): $1,000Garbage removal: $4,000Radiant heating.... only applies to 3 units in the basement, so not comparable.

For outside drainage there is a slight V at the door entrance. 

Exterior paint, new windows, new concrete ADA pad for 2nd entrance.

Many of the properties we have looked at have separate levels and/or entrances so it works great for our partner to live at the property but still have seperation from guests space and main home. 

@Francisco Lara bring 2 pots of coffee and go to the Home Depot contractor entrance at 6am and collect cards/contact details while handing out free coffee to contractors.

The law requires you to give notice of entrance; it does not require you to get permission.

@Theresa HarrisIt's pretty much a triplex with the third unit with its own side entrance, we are using it as a duplex to avoid dealing with an additional tenant.