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

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.

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.

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.

Here are some of the highlights: quickly set up bank accounts for each property and sub-accounts under those for things like security deposits and CapEx; virtual credit cards tied to each property; quick transfer of funds; ability to send money back and forth to tenants (some platforms are for collection only but won't let you send your refundable deposits back to your tenants); easily categorize every transaction into IRS Schedule E categories for reporting taxes; ability to split transactions; tenant management from vetting to drafting lease agreements to collecting rent.

BASIS FOR YOUR AS-REPAIRED VALUE (ARV): When you flip a house, it’s important that you know what you are going to sell the property for.

Yes you can sell to investors with tenant in place.

Reach out with what you are trying to sell and I will see if I can help you find a buyer?