You should connect with @Brie Schmidt as she knows and understands the Chicago zoning laws, but my gut instinct would be that you would be better served looking into a duplex down scenario.

Do you even know why investors create an LLC, or multiple LLCs?

Just know that if you are moving somewhere to chase the hot market, it will only stay hot for so long.

Yep I know it- I've had multiple tax clients over the years face a mean surprise with that. 

Like any tool, you have to know how to use it correctly or you could get, "injured".We use it to quickly sift through multiple options - and that's about it.BP has a Rental Calculator that includeds everything you are asking about: mortgage P&I, property taqxes, home insurance and percentage for maintenance & vacancy.It also includes Cap-Ex percentage, but in our experience it's a waste of time to worry about this.

@Roshan K.Ya I know it looks sketchy and defeats the purpose of the LLC but I figure if I kept the funds seperate and can prove that they were used for business purposes only it wouldn't be so bad as a temporary fix.

I don't see students paying Ivy league for this school, but I could be wrong, I don't know this school at all. 

So far, we have shortlisted Columbus, Orlando, Indiana, Vegas and Rochester.we live in Toronto and we really would like to connect with people like us who already started their journey to know about their experiences and insights of investing in the US! 

Now, we own 65 apartment units and 80,000 SF of commercial warehousing.Let me know if you have specific questions. 

You can also contact a local alcoholics anonymous or other organizations and let them know you have space available for anyone living sober.