Already own but looking to get into investing

[Kenneth Marks]

My husband and I are both 31 years old, live in Chicago and are interested in getting started with real estate investing. Unfortunately, this was more of a recent discovery and we are just one year into our 30-year mortgage on a $349k 2 bed 2 bath condo. We're not sure if the best move would be to sell our current place to buy a property that we could live in for a year and then rent, or to somehow just buy another property.

Since we only put 5% down on our condo, our total monthly incl tax, insurance, HOA is $2246. Since the market rent in our neighborhood is slightly less by about $200/mo, I don't think it would make sense to keep our current condo and rent it out and then buy another place. Selling might not be a horrible scenario, because the market has done well in our area over the last 12 months. Zillow and Redfin currently estimate our home value around $369k.

We also only have about $20k in cash that we'd be willing to part with (a lot invested in stocks), so not a huge upfront down payment, but we make $270k combined annually. All of these signs initially tell me that we aren't well positioned to get into real estate investing at this time, but I don't want to make that assumption and shut the door on investing if there are some realistic scenarios we should explore. 

I appreciate you reading this far and providing any help you can. Happy to answer any questions that might make it easier to guide us. Thanks again!

Ken