Wanted to bounce this off someone as a first step, please.Rental property has about 6 concrete stairs (carriage walk) going from the street to the sidewalk. 

The one-car, detached garage--to my eye, a carriage house--may extend across the property line. 

I painted and stenciled the bathroom floor in my carriage house because there was no salvaging the hardwoods.

You never know when that pumpkin will turn into a beautiful carriage. 

So I had this crazy idea that we could renovate the house putting in a 2 bedroom/2 bath apartment and also remodeling the carriage house on the property into a rental unit, and we could probably sell it and not lose money or at least have an income property were we could rent out the 3 units and we could move and my son could rent one of the units while managing the other 2. 

Regardless of where you live and its price point, that's often putting the carriage before the horse. 

Narrow paths encumber carriages and wheelchairs, and properly cleared pathways ensure flow and safety of pedestrian traffic.Remove ice to bare pavement or make as level as possible and treat with sand, sawdust or similar material.Please clear any snow that may be blocking a handicapped ramp, fire hydrant or catch basin.DON'T: Shovel or plow snow into the street: Violators caught shoveling snow from private property into the street will be fined.Overexert while shoveling: Excessive strain from the cold and hard labor may cause heart attacks.

It is 6 bedroom 3 bath rents for 3k a month and behind it is carriage house  that has been renovated and is 3 bedroom 2 bathroom.

My triplex is actually 2 units in the main house and a carriage house, so I insure them separately for liability.

Kind of like putting the horse before the carriage.