If you see at least a few zoned in the designations you mentioned above, that's potentially a good sign that you can get support from the local Alderman's office, and approval by the ZBA (zoning board of appeals), to rezone.

You are roughly 50% completed, the interiors will cost more than you think.

Even a single family builds can vary significantly based on site conditions and required structure/design.

Also, focus on 2 years of job/income stability.Section 8: This is the Property Class S8 was designed for.

The interior is a total gut: new insulation, sheetrock, plumbing, electric, kitchen, bathroom, doors, windows, and landscaping.

I've owned the house for few years and have spent a lot of time trying to design an addition to add value to the property, but the current floor plan is really not conducive to realizing a return on that investment (tiny living room, low ceiling basement, poorly placed basement stairs, etc.). 

Instead of debates and personal opinion, look for proof https://www.ladbs.org/docs/default-source/forms/plan-check-2017/single-family-dwelling-duplex-plan-review-list.pdf under G (Interior Env) which defines the minimum requirement of a habitable room (aka bedroom or bathroom).

. - This is not something to 'fix' - the system was designed that way.

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