I will be living in the guest house, while renting out the main.Both units are without washer and dryer units, my question is, do I supply them in the main house; or let potential tenants figure that one out?

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

I don't know if that is included in the total rent numbers the owner supplied. 

I'm not familiar with Canadian regulations but you should look into how you can get access to money if you don't have any.

IMO, the best strategy for that type of individual is to purchase residential property in an area they are or can become familiar with; in an area where the neighborhood is “on the rise”, typically where demand exceeds supply and people are spending $$$ on fixing up properties.  

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

Dig and remove around 200 square feet of an old concrete driveway, frame and lay down the concrete (concrete will be ordered from concrete supply business) and complete a brick ribbon around the driveway.

Find the style that people are doing in the area then find equivalent options for materials at local supply houses.

Seems a bit high on the exp ratio near 43% but we do pay a premium for our solid cleaning lady, she also stocks supplies, runs errands and other duties for no "extra" charge.

There is extra costs, more regulation, and more liability.