Your not correct under many different circumstances.First property tax is 1.1% (fairly safe) with 2% annual increase (prop 13).Next expenses include a lot more than property tax and interest. 

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

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.

And thats not including how long it takes.

Continue renovating my current house--big projects would include finishing the basement (adding a bedroom/bathroom/living rm space) and putting new siding on (the current siding is probably the original).

I appreciate your insight on starting with a fourplex, house hacking, and the importance of building a solid foundation early.

Property includes: (2 buildings)The large old building with main level office previously a dental office and potential for build out second floor of (1)-1br efficiency apartment, (3)-2br/1bath.

you just input the address and it import the information which has bedrooms, bathrooms, and square footage. just be careful with the insurance and property tax data.

A few other houses (all single family houses) on the same street are on the market for rental and they (including my house) all get grouped and nestled under one cover listing as “units” of an apartment complex.

Upgrades included modernizing interiors, updating plumbing and electrical, and enhancing curb appeal.