Is house-hacking a condo in Chicago a feasible option to begin with?

Understand all of your financing options before getting into it!

If you post your inquiry on there you should get multiple options.

I can increase my cash flow to $500-$1000 since I will need smaller loan.Other option I have is I can move into the new build and rent my existing property and cash flow $1000 a month. 

They look like a good option if I can't find another property.

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thats always an option..

The other option would be to purchase a property with some value add, spend the year rehabbing the property and then refinance out into a long term loan after the work is completed and rates have fallen.

There are not many multi-family options available in my local area, and the ones that are available are overpriced or the current rent rolls are extremely below market average($200-$400 per unit).

If that option is not available then I will look at shorter terms.