I would like to pull $100K from the property to address some urgent items.

A good property manager will be able to help you with this as they should have a good pulse on the market for the aesthetic demand of things.Also, you can ask your contractor if they have someone or work with someone who aids them with design of things.

Some items about this analysis:- 18% over 10 years is only 1.6% annually.

These two items can result in extremely poor returns if the purchase happens to coincide with a period of modest or worse appreciation.  

Realize cap expense items are very costly.  

A household with more than $1MM in net worth excluding their personal residenceThere are some other options and more details, but if you can check either of the items above, you are safe to call yourself an accredited investor.The more complicated designation is the Sophisticated Investor.

@Emma PowlinAny contractor can give estimates for remodeling, but does the contractor know/understand the unique paperwork, compensation structure, draw request process, change order process, allowable items, required items, etc.? 

Would condos be a better option to avoid high ticket maintenance items like the roof and garages, landscaping etc?

@Jay Hinrichs I know the video is short, but I'm interested in your opinions on the actual 'rehab' items that can be seen - and any feedback overall.

Lots of differences you are seeing about Chicago compared to elsewhere and I will share an ebook we created to help out of state investors get some insight on huge items we see a lot of people miss when coming into this market.