SRO. single room occupancy. are in HIGH demand with populations who are getting served by DHS-dept of human services. think of domestic violence, homeless, exiting or enter jail, prison, rehabs -for physical or mental reasons -accidents, surgery, breakdowns etc.; divorced, teens exiting foster care (18-21 age). yes there is a need. you need to know where your clients will hail from. there you will find them at DHS/DSS/WIC/DV/ agencies. single rooms, shared kitchen, bath etc. all very commonly used for "temporary/shelter care" housing. for 30days to one year. pending --usual things like court hearings, sentencings, adjudications, or pending finding a larger unit to reunify with children taken by CPS. be ready for drama. but if you work it hard-the state/county/federal will pay.

From what I have seen, section 8 inspectors focus more on hazard/safety items than cosmetic issues in the property

He didn't know his insurance lapsed over the summer, and his son was injured requiring hospital attention--his son broke his leg and it required surgery to fix.

Was interested in a $50K HELOC to have the plumbing fix and do some cosmetic updates towards the end of the year, when I'm preparing to put the house on the market. 

A home in chicago proper that is only worth 24-35K will usually require over $100K of work. 8-12K assumes the cheapest cosmetic rehab, but it doesn't work in the city because the buildings are too old.

We are definitely looking for something that is move-in ready, or needs minor cosmetic work.

When was it (they) replaced.The above items are more than likely the most expensive repairs you'll have to make on a property so it's good to know when and if they've ever been replaced so you can plan / offer accordingly.The cosmetics don't matter as much i.e. flooring, paint, etc. 

For example, a next door neighbor's house came up for 99k with only minor cosmetic work needed, would be a great LTR investment bringing roughly 1200-1400/mo.

While this property needs a significant amount of cosmetic rehab as the plaster has all been removed, renovating 3 units would be a pretty costly.

The first few need some work, mostly cosmetic.