If you like a market, just get a base hit deal there and start spending time at the property getting to know the house, the market, and local vendors.

On the other hand, I invested in other areas, Humboldt Park, Pilsen, etc. which I thought would appreciate, and did not - or would take much longer to do so.The problem is I have had a hard time being honest with myself, and basing my decisions on wishful thinking, not cold hard facts. 

They do tend to require more time managing and ensuring that your rental rates are competitive based on current STR availability/rates in your area.

Investors typically grade areas based on a lettering system A-C/D.

Be careful of someone that wants to "partner" with you and ask you to use your credit.Can be a good idea, but only if serious partnership agreement created by your attorney (not theirs).You can also start building your network to find opportunities to refer out and learn from.Per this NY Times article, the average American knows around 600 people.https://www.nytimes.com/2013/02/19/science/the-average-american-knows-how-many-people.html#:~:text=The%20average%20American%20knows%20about,do%20you%20know%20named%20Kevin%3FPer the US Census Bureau, the average American moves 11.7 time in their life, which based upon an approximate lifespan of 84 years, works out to be about every 7 years.https://www.census.gov/topics/population/migration/guidance/calculating-migration-expectancy.html#:~:text=Using%202007%20ACS%20data%2C%20it,one%20move%20per%20single%20yearSo, if the average American knows 600 people and they each move about every 7 years, that means that the average American knows around 85 people that move in any given year.How many of those moves do you want to be involved in?

I'm basing this on what I've seen in agricultural investing in Central and South America.

Lastly..Gang seriously.It is frustrating how much proof I constantly need to post yet so many of you are so invreddibly stubborn so see what is right infront of you, and make decisions based on emotion/opinion, instead of Proof, Data, evidence.It truly is up to you.Want to keep struggling?

While it is also true that Chicago leans tenant friendly, you can mitigate a lot of that risk by investing in areas that have a stronger tenant base.

 Continue buying, keeping some and flipping Anything in my market where the net cap is 20% ish based on cash purchase. 

They can take out enough for a down payment for the next house and a little extra to put into savings as a "What if" fund maybe 3-6 months PITI based on the new home payment.