@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.

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.

Those holiday numbers are a bit low, those daily numbers are a bit high. 

The "+/-" isn't based on the high or low end of the sq ft range, it's based on the differences in quality, or finishes, or the specific location within that micro-market. 

You should find out what percentage of the rent is being paid by S8 and by the tenant.Tenants have to sign the rent increase and some won't because they don't want their payment portion increasing.It's also highly unlikely a S8 office will approve the huge increase from $797 to $1300.- BTW: the $1300 includes all utilities being paid by the landlord.

I am a 24 year old who's employed in the CAF and looking to getting into real estate, more specifically BRRRR.After looking online for quite some time I've noticed how high Canadian real estate is and I wonder if it is even worth getting into.

Strong rental markets with low vacancy rates are ideal for long-term holds, while areas with high ARV growth are great for flips.