Generally speaking these rules are easier to attain in secondary markets and blu collar neighborhoods.

As long as you don't need the cashflow, you might be able to break even or maybe lose a little money month-to-month but effectively earn ~$400/month in loan paydown while hopefully attaining some appreciation.You should still double check the terms of the loan. 100K purchase with 12K down is a loan of 88K.

I'm hoping to attain a portfolio of property that will provide sufficient income to grow old with grace.

I am very happy to see you have set attainable goals that aren't so ridiculous to those of us that have been investing or straight out of the mouth of some "GURU".So I applaud you for that.As to finding other investors in Chicago that are doing what you hope to do, have you hit any Investor Clubs yet?

As @Shawn Holsapple  indicated,  your targets are attainable.  

I am attaining my brokerage license in the next month so that I am legally permitted to assist with leasing, management, or new brokerage opportunities.

I suppose a more pointed question is whether or not it is possible to attain this goal by purchasing a run-of-the-mill turnkey property at retail, every year for 10 years, in a stable market like Indy and applying all excess cash flow to principal reduction.  

would you suggest in person vs online for attaining a real estate license?

Would having two names on the loan negatively affect our ability to attain more lines of future financing in total if the loan was filed as an individual?

@Jackson Wells Welcome to the site, very attainable goals, good luck