However, I need to liquidate assets and I'm exploring the idea of selling one or both properties to an investor.

Numbers don't pencil out for a 30 year mortgage, but property still sells! 

However, when you sell the home, you will owe 20% of any appreciation on the home in addition to whatever you borrowed.My intention going into this was to house hack for a year or so and then refinance.

If you plan on renting it when you exit the project instead of selling, you could do a cash out refi at that point using something called a DSCR loan.

Jackson and Washington parks are always a huge selling point, as well as the proximity to university of Chicago. 

The property owner doesn't owe me anything, but within the next 5 years he will have to sell to me or renegotiate with me.

I'll never sell this property. $ for $ match is easy.

If property values fall and you are forced to sell you would be wiped out.

Will it cash flow in year 2-3, or will I need to sell after I move out?

Exit Strategy: MFH can present challenges when it comes to selling compared to SFHs.