We have a SFH in Clairemont/Linda Vista (area code 92111). 

I am aware of current Chicago proposal to more easily legalize garden units and this space looks like it would pass all code requirements or only need minor adjustments.- Order of repairs / updates (Musts vs Wants)?

Otherwise google “building material surplus” / scratch and dent” and your ZIP code

If your strictly looking for work horses with mild appreciation Memphis B+ and A-Class areas would be a great investment tool.

@Pete Panci zoning and building code for ADU's is tricky here.  

These are professionals with additional training and a stricter code of ethics.

You can usually go on the housing authority website and look at the allotted rent amounts per zip code per county.  

Keep in mind you will also have to deal with the Régie du Logement, which is quite strict on rental increases.From what I've heard, deals in Montreal are rare and if you manage to find one, you better be the fastest man on the planet to make an offer cause they go fast.

However. as long as you have a line, neutral, and ground wire (3 prong fittings), installation is cheap.NEC Guidance: https://www.ecmweb.com/national-electrical-code/code-basics/article/20898894/nec-requirements-for-groundfault-circuit-interrupters-gfci

In witch zip code is the property?