Do you plan on living in it or is this for investment purposes?

This will help some in planning for cash flow.

I love the plan of getting an STR in FL. 

Depends on what you plan to do with it.

I just want to make sure there isnt an alternative I have not thought of due to my ignorance in my research since I was initially planning on residential. 

Early failure is when hings don't go as planned at the start of something new, like a project or a job.

I pitched it to my fellow investors, but numbers did not work for them and we did not want to purchase the house ourselves, our initial plan was an assignment.As time passed we decided this house needed to be listed on the MLS to get a retail buyer.  

I like that plan, I just don't know how many properties my wife will let me have with negative cashflow each month! 

If so, you could plan to market about 60 days before lease end or even sooner if their house is ready earlier, so you can close as soon as they are out.

All of Chicago is not falling to pieces with crime.I'm happy to connect, understand your goals, and see if we can add value to your plans.