2-flat Listed As SFH

[Gian Carnero]

Hello all, This is my first post so bear with me. I'm in the early steps of purchasing my first home to be used as rental income and it happens to also be my first property. The property is in Chicago, has a first floor 2B1BA and also a second floor with the same 2&1 and an unfinished basement. There's separate water heaters, furnaces and separate utilities along with a front hall to separate the two units. The thing is the house is zoned and being bought as a single family home. Here's some of the questions I have about this situation: -Will it be difficult to have it zoned as a two-flat in the future when/if I plan on selling? -What is the process like requesting permits for changes on the property? -What kind of risk/problems do I face renting out both properties? Insurance? Leasing? -Will I face any problems come tax time? -Anything else I'm not taking into consideration? It seems to me like I can proceed to rent out the first floor unit and the second floor unit as an in laws unit and keep the house as is. Yes? No? I'm open to any and all interpretation and appreciate in advance any insight anyone can give. Thanks again!