Chicago Rookie Investor needs your help!

[Tomas Saenz]

Hello, I hope everyone is doing well.

I'm at a crossroads in my investing path and would love the advice or views from other investors.

I currently own 3 properties in Chicago:

1. Duplex in a C- neighborhood  south Chicago 

2. SFH in a c neighborhood south Chicago

3. A fixer future flip/ or long term hold in emerging neighborhood Avondale 

I work a regular 9 to 5 and most of my money is currently being funneled into the Avondale fixer. So basically I'm not able to save a significant amount to put down a down payment on my next place. My other properties are rented out and covering their mortgages ( all 3 purchased with conventional financing).

I'd like to start buying in more established neighborhoods like Avondale for example. I am not opposed to selling my 2 properties in C class neighborhood's to achieve this however if I could hold them that be great. The goal is to start snowballing these properties into larger chunks of wealth sprinkled with some appreciation?

Curious, what you would do? Open to all strategiesThanks!

[Soh Tanaka]

Think in terms of how much equity you have in your current rentals first, and then figure out what kind of return you are getting now on your equity. Compare that with new properties you are thinking about buying and see which one gives you more cash flow per equity. That's one way to look at your situation.