There are pitfalls in the entire process...from sourcing, analyzing, scoping the repairs, doing the repairs, leasing the property, managing it or flipping it, how you do those things ultimately can make or break your investment goals. 

If you want to be passive in RE, then  start with NNN leases or (if you have some money to invest) syndications.

I've had trouble finding a standardized parking lease for Chicago. 

Make sure you have a strong lease and a cosigner, and you'll probably do fine.

The property is right across the street from a college and stays 100% leased all year at 700 a month each side.

Limitless Real Estate Group LLC - Property ManagementWe handle every aspect of realty management - General maintenance and upkeep- Demo and rehab construction- Lease processing and renewals - Tenant selection- Screenings, background checks, deposit collections and lease agreements- Property repairs- Rent collection

As long as you properly screen tenants and set up the lease properly it will work out.

I only buy if it cash-flows now and there is enough delta in the mortgage vs lease payment to whether any storm. 

They did give me leases to look at, but there were some other issues that arose to the point where I was uncertain whether I could make the deal work.Thanks @Ben Day.

(Wholesaling, Lease Options, Subject To, Short Sales, Loan Mods, Wrap Around, Owner Financing, etc.)