I'm taking my first baby steps into Rental investing in Chicago.

I think your first step should be partnering with someone that has done this before.

Good luck @Sarah SmithI’ve bought about a dozen buy and holds here in Vegas and have yet to sell one as I haven’t found the “next step up” please let me know what you find if anything. 

You're too nice.Today, you start the first step of eviction for holding over in your area.

Currently a single family home (pictures online look horrific), but approved for condo What steps should I take before calling the owner?

I know it has not been easy and I'm sure you can say the same but now I always try to tell myself not to let my fears control my life and you being here is a step in the right direction.

There are more resources on this site than you'll ever need but one of the biggest steps is just getting started.

However, I'd argue that there is no more risk in holding than there is in pursuing hard money and ending up not being able to refi out.I'm sure there are those that would say sell and pursue private money or hard money, but if monthly cash flow is $300 or more I'd wait it out.

The 401k protection you mentioned applies if you were in a car accident, for example, and someone wanted to pursue your assets. 

Now I want to keep going but I am unsure about my next step.