Agreed, I would feel the most free and secure both mentally and financially by selling the property.

TLDR: Mentally it seems better to try and invest locally.

Overall I would prioritize cashflow over appreciation.

I believe that's backward, because that mentality fails to acknowledge psychology.

And if you are on Bigger Pockets, you already have those mental attributes.Are there any work arounds? 

I have little knowledge of the city, and want to prioritize an area with decent schools, that will hold up well in the rental market.

It was you who presented this concept as I caught this bit while I was driving in my car and made a mental note that I must check every future deal on this.Yes, I was asking if distributions are Return on Capital or Return of Capital.

Given the state, location (Chicago) and mental, that I am in, I was wondering what would you all suggest as my first steps on getting into wholesaling in Chicago or nearby cities/states.As of now I don't have my RE license so I know I am limited to 1 sale for the 12 months in Illinois, so I wanted to see if maybe this first sale can help:1) identify if wholesaling is for me2) Build capital for my first home purchase (MFH) since I am still with my parents.I have attended local meet ups and have noticed partnering or maybe potential Joint Ventures can be an option, so definitely opened to any suggestions/advice.Thanks in advance!

You will find more things to adapt to once you are building You have to be ready mentally for these events.

I think mentally I want to believe the easiest part is the appraisal and should not take a month like the home I'm selling now.