The property taxes in Indiana are very advantageous for investors, while the Chicago property taxes will crush your net cash flow - which is what your main focus needs to be.

Should I get an apartment first and wait to invest or should I take advantage of my VA loan and allowances as soon as the opportunity presents itself?

There are advantages and disadvantages to each option.

In addition to the other advantages I mention above, meeting lenders who regularly attend local real estate clubs, face-to-face, is the safest way to avoid an online scam.That there are those who must rely on the web for their commissions is not Brittany’s problem.

Fix the steps, but don't let the tenant take advantage of you either.

So, what is my advantage?

Take advantage of EVERY opportunity!

There are great conventional loan products that have the similar down payment requirements but could be more advantageous cause it will not require a refinance to get rid of mortgage insurance.  

The only requirement is that you disclose you are a licensed agent, so the "knowledge" you have is disclosed and it is never misconstrued in court as an unfair advantage. 

I think there are some great options for you with the house, but I want to make sure that all of the advise you get it sound, possible, and legally advantageous instead of giving you some ideas that sound awesome and lead to more strife.Blessings in your process, Eric!