It sounds like you started investing, but didn't follow all the way through.

Logan Square, Pilsen, Avondale look and sound good on paper but that is where everyone is looking.

You live in NYC and are close to so many areas where you can make a more sound multifamily investment.Most of my holdings in my life have been in NY and the landlord-tenant laws never were much of an issue because of how I chose tenants, but it's certainly a consideration.

Agreeing to dates in advance sounds good, but what happens if you cannot agree?

That would certainly allow you to sell and do a 1031 exchange with just your interests.In your situation however, it sounds like you have each taken title to one of the properties. 

You don't sound like you want to do the work of a landlord to be honest.

@Luis Herna, while I am not overly certain about TX's nuances, but they sound similar to Ohio, if you are collecting a commission, whether a fixed amount or a percentage of sales price, you are brokering deals and require a license.In my market the grey area solution is, like Daniel noted, actually close on the deal in a dual closing transaction, or formally assign the contract with an assignment fee tied to it.  

It sounds like you have a great plan for entering the real estate market, and a duplex or small multifamily could be a great way to house hack, saving money while building  equity. 

This setup sounds like it could work well for you!

You will need to disclose to your lender if you cannot find a replacement tenant.Can you DM me the property address?