Non-Conforming Garden Unit in Chicago

[Bree P.]

Hi All! 

My husband and I are looking at doing an off the market deal on a multi-unit (two flat) on the north side of Chicago with a non-conforming garden unit. While we own a single family town home in DC, this will be our first multi-unit. I was hoping to get some insight on a few things from some of the seasoned folks out there. 

1. Considerations for not using an agent: We plan on hiring our own real estate attorney as well as finding our own inspector. Anything else we should consider doing? Any recommendations on either front?

2. Property management: while we plan on managing the property ourselves while we live there (my husband is in the military and we just started a 3 year tour in Chicago), we may look to a property management company to help maintain the property when we move (depending on our tenants and how the numbers shake out). Will a property management company rent out a non-conforming unit? Does anyone have experience with a similar situation?

3. Rent: do those of you renting out your units increase the rent on an annual basis? We are used to the 2% rent control limit in DC and haven't touched the rent for the past few years (same tenants), but wondering how folks handle that. 

Thanks so much!

Bree