Without trying to sound like a dating website, I’d love to connect with like minded people on their thoughts and views of the industry and different markets - either in Chicago or elsewhere. 

You're making it sound like it packs its bags and never comes back. 

If this sounds like it's doable, then I'll need to find one and get the process started.

If that sounds too risky get a 50% loan, use it for a downpayment on the second property also with a 50% loan. 

The bottom line is how you decide to split the profit is completely up to you and this new partner.

Your strategy of converting the garage into an additional dwelling unit (ADU) and using the property for short-term rentals (STRs) sounds like it has paid off well, especially given the unique aspects of the property and its location.Your approach to identifying a unique investment opportunity that was overlooked by others, and your patience in securing the right deal, are key takeaways for anyone looking to invest in real estate.

It may sound nice to pay a 6% management fee but the extra fees can add up to be more than the other company that charges 10% with no additional fees.

The definition with them is completely different and has nothing to do with the amount of days you stay there.I hope I'm not coming down too hard here but sometimes the tone of typing out a response is hard to convey.  

To avoid paying capital gains on the sale of the rentals, the most straightforward way is to complete valid 1031 exchanges on your two sales.  1031s themselves can be a little unintuitive to navigate. 

It sounds like your tax advisor should have included the depreciation from the cost segregation study provided by Capital Square.