I know there is no one right answer and some variable, but looking for ideas/advice. 

It is hard but as a realtor I pay attention to prices throughout the year so that I have an idea of whether or not it is a "real" discount.

I don't think you're being too ambitious, I think its a very smart Idea especially in Chicago where there are an abundance of 2-4 unit buildings!

I like the photo ideas!

Quote from @Erick Pena: A "good" rental property is one that covers all expenses (mortgage, taxes, insurance, maintenance, property management fees, and any other costs) and still leave a surplus (commonly referred to as cash flow).Calculate cash flow as: Cash Flow = Rental Income − Operating Expenses − DebtThere's much more to it, but that's the basic idea.

I think all of your suggestions are great possible ideas to do this deal! 

I have been seeing ideas for investing in a laundromat.

Do you have an idea of the type of property you want to buy and a price range?

Again, the BiggerPockets store has some books on this topic, or you can learn about it by watching podcasts, reading blogs, and interacting on the forum.

The idea of getting a duplex seems great, but I am having trouble finding anything on and off market.