That is how I got into it almost 20 years ago in Rochester & it has afforded multiple additional purchases & "practice" in this line of work, all while maintaining a regular full time job. 

@Jonathan Polanski The agent might be trying to buy for himself (conflict of interest), trying to keep the entire commission (horrible business practice), has had a bad past experience with your agent (unlikely but possible) or has a preferred investor lined up. 

I simply work to add value to a property by improving it, and then I realize those profits.

But plaster builds up REAL fast, more than 100 sq ft is beyond the practical, and you'll need to pay for either a dumpster or a hauler. 

It sounds like the Chicago opportunity is to buy a value add opportunity - which will take capital and expertise to make improvements. 

Upon further though I decided to wait to increase rents until I had improved the property more sufficiently.

If it takes you 5 years to recoup the money you put in to that improvement it's probably not worth it.

An improved rental?

I've been growing my education in RE for about a year, and my wife and I have been actively looking for our first deal for about 6 months now.While we wait for that first deal, however, I want to make sure I'm also continuing to invest in gaining practical experience that will help that first one be a success!

And you possibly over improved the house .