Just like in any task in life, starting without any plans will likely end in unexpected/unplanned results, very likely failure. 

.- Original siding (fiberboard) not maintained and allowing pest's to (rats and squirrels) egress in and out of the units.- Caved in celling with open access to attic, from roof leak that went unfixed for 3 years.Most repairs were sweat equity.

Just had to repair a leaking roof (8 years old) on one of our rental properties, Squirrels got into the 30ft Al ridge vent (not in one but a number of places) & loaded it with nuts etc.

If you have not accounted for potential future "Special Assessments" to address deferred maintenance or simply unplanned repairs, it could significantly impact your deal.

With that being said I would like to continue my multi-family investing career but was looking for advice going into a new market (Chicago).If you are a multi-family investor in the Chicagoland area, can you provide advice on unplanned expenses or different ways to think about multi-family deals and deal structuring in the Chicagoland area?

It would attract starlings, pigeons, sparrows and squirrels. 

Plus --- being overleveraged at the front sounds great for now, but when you need to refi, or pay off that second, unless there is a value add, there won't be enough room and you'll have the unplanned need for cash rather than handling it on the front end and having that equity to play with.

Otherwise, you can simply get a job, but that's not usually going to bring in enough to squirrel away to invest.

Plus during your commute and workouts, list to podcast and during your lunch break and 6 hours of "unplanned" time read books, lots of them!

Since then we've had the good (and unplanned) fortune of rents growing quickly, upon closing our rents are 21% under market.