The second home is a few blocks away and also has a large yard requiring tree removal and minor clean-up to look good....Its a 2BR/1BR brick faced range with an enclosed breezeway with entrance door/jalousie window separating the house from an attached garage.  

It has a basement apartment with separate entrance and driveway.

Is it possible to get a permit for an extra kitchen within the main unit and an exterior door for entrance that they would 100% accept?

@Robert Durden Depending on where in the area you buy, some homes have walk-out basements and some have rear entrances.

The back porch, which is in front of the main entrance, is flaking and chipping off.

Just across the street from Buckley AFBs south entrance.

I've seen clients live upstairs and rent out the basement on Airbnb, so you get the best of both worlds, privacy and your own space while the lucrativeness of Airbnb, so you can definitely live for free or close to it with this strategy, but you have to know which areas allow Airbnb after you move out, and it is a good idea to have a 2nd option if the city or county changes their policies and you Airbnb anymore.3) Combination- you can easily do both strategies if you find a house with a walkout basement or separate entrance to the basement, and if you are willing, you can Airbnb the basement and then rent out the rooms upstairs.

In the triplexes and quadraplexes we shovel common areas, but tenants are responsible for their own entrance walkway and steps.Anything 6+ units, we handle all the snow removal.In the smaller properties it depends on what you negotiate in the lease.  

It has a basement apartment with separate entrance and driveway.

Initial complaint is that the master is cold not sunroom but stems from heat escape and air entrance from sunroom.