I am looking to acquire property to generate passive income to put towards a retirement plan.  

I NEED TO SAVE!

Also have about 2000 saved.

Over the past 6 months I have been saving money for investing and researching everything I can about investing.

I know how it gains you access to the MLS, networking opportunities, increase legitimacy, and save money on commissions (when I do a fix and flip).

My Fiancé is a broker so we are saving on a lot of realtor fees.

Below I have compared 2 examples of selling traditionally with a Realtor at 6% commisions (which it may be less as it is negotiable) vs selling with opendoor or similar service.Comparing Opendoor to a Traditional Sale with a Realtor$400,000 Home via OpendoorHome Value: $400,000Sales Price: $375,000Charge 12%: $45,000Commissions 7%: $26,250Total Costs via Opendoor: $71,250Net Proceeds to Owner: $303,750$400,000 Home via a RealtorHome Value: $400,000Sales Price: $400,000Traditional Closing Costs 3%: $12,000Commissions 6%: $24,000Total Costs via a Realtor: $36,000Net Proceeds to Owner: $364,000In this Example Selling with a Realtor will save you $60,250!!!

Although house flipping and BRRR have always seemed interesting to me, I've fallen into a couple opportunities to do those, with minimal risk, but also minimal effort.The first home I purchased was '06 when my son was born that I rehabbed with my father (a retired contractor).

I have a FT job that I intend on keeping for a while but I would love to retire in 15-20 years rather than 30.!

As a very new investor living in Chicago and currently working to save money to afford an investment property, am I better off not trying to invest in Chicago?