Would it be beneficial to wait for the "home run" or to use different parameters and get a "base hit".

I think applying your existing skills and experience is some times one of the easier ways to get involved in the Chicago real estate game!

This was my starting point to really get into the game and not only see how things work first hand, but it also inspired me to keep going.

Do some data-based analysis to determine if this investment makes sense as opposed to emotion driven decision making.

I’m excited to learn and evolve from you all and I’ll glad accept any words of encouragement and helpful resources as we start out :)Have a lovely day all!

Think like company like homes or zillow or local exp team that could offer a very efficient buying process thus could offer more attractive buyer commission, especially at expensive home price above 1 mil area, that would impact heavily on heavily-dependant commission based broker. 

I'd make sure the agent you're working with knows the campus and STR game.

So I require skin in the game (average is 5% to 15%) to offset this.

My guess is there isn't going to be a clear answer based purely on math and analytics, so what makes the most sense for your current life and your future goals? 

I am not directly working with him (I am based in Boise, Idaho) but have connected him to a solid lender and a investor friendly realtor.