Prices remain relatively low, but appreciation may be slower.Monroe: A mix of cash flow and appreciation potential, Monroe has become a popular choice for investors, especially in areas where new developments are popping up.Appreciation-Focused NeighborhoodsBallantyne: A well-established area with high demand, Ballantyne offers excellent long-term appreciation potential, though cash flow opportunities may be limited.South End: A booming urban hub with a vibrant retail and restaurant scene.

I am in Florida and we have a strong STR market and most of my buyers bought at high rates and using AirDNA we were pretty spot on for the numbers and we were successful in being profitable.  

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

However, turnover is high, probably because privacy is hard to come by.

I am assuming here, but if it's been on the market so long, it's priced too high for it's condition. 

I get FinTech is a high-risk activity, but imagine the industry will consolidate to one or a few strong players.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

While this is a great and highly motivating goal, most people are either clueless or incorrect in their belief as to what is required to obtain this “lifestyle”.Understanding of the “how to” get there is further obscured by the misleading, and often patently false “pathways” sold by real estate educational MARKETING companies as workshops, upsold to association memberships, upsold to mentorships.

My recommendation would be different if you were a high-income earner or if you wanted steady equity growth.