Hello, I am looking to get started in my Real Estate career by building a 3 Unit Condo complex on a lot that I already own in Chicago. 

Messing up on your 50th deal will probably not kill your investing career.

Now we just need to ensure there's nothing too glaring post inspection and that the home will be suitable for FHA post-flip. 

Most towns don't allow you to open a business or store front anywhere you want - it has to be in areas they (the town) have deemed suitable for commerce, whether you're a Salvation Army or Walmart.

But is in college and plans to stick with his career.

I’ve reached a point in my career where my earned income is flowing a bit easier and more than my family really needs to live comfortably.

What you want is a career that will pay the highest possible income to be able to get financing for investing.

What would be a good career to pursue that would best lead to success as a CRE investor? 

My goal is to scale up to as many units as possible over my Career and I have gone from 0 units in 2013 to 14 in 2017 (12 now after selling two single family).

I am about to start a secondary career as a RE Agent which will get me a lot of exposure in my local market and a lot of experience in RE in general.