November to March tends to be the slowest leasing period so you are likely fighting that battle, but if you aren't at least beginning to receive more inquiries or having showings without tenants at minimum interested in a mid March/April move-in there are two potential issues: the home is over priced compared to competition or the property is inferior in condition.

For those actively investing in Chicago, how has your mentality and strategy evolved compared to previous years?

For a 2 unit, an appraiser will rely on comparable sales, but an investor looking for cash-flow may care more about income.

You just need to have more reserves set aside compared to a single family.

Quote from @Evan Murphy: I agree with Davids point of considering where you want to invest compared to where you live.

You spend a lot of time and money having people do this work, and at the end of the day you don't net any more income compared to a long term rental.

Lower entry point compared to NY, 3.5hrs away.

If you turn any two "bonus rooms" (rec room, office, formal dining room) into two more bedrooms, then you're at $5,950+ per month—a 138% increase in rental income.Now, imagine scaling this across multiple properties while keeping lower upfront costs compared to multifamily properties.

Co-living is seen as a non-financial tool to encourage deeply affordable units, serving as transitional housing along the housing continuum.A study by Gensler and The Pew Charitable Trusts highlighted that adaptive-reuse co-living spaces could offer more affordable housing solutions compared to traditional studio apartments.

These can bring in significantly higher revenue compared to long-term rentals, especially during peak travel seasons​.Single-Family Rentals in Growth Markets:Target neighborhoods with growing populations, good schools, and job opportunities.