Deploy your VA mortgage / house hack while you go to school, and work part time? 

Taxes are low, communities/schools are good, multiple types of transportation to the City, and many people who work in Chicago live here.Best neighborhoods for your price range: Highland, Munster, Griffith, Schererville, Crown Point (a bit further from transportation), Dyer, St.

Have an agreement about how to split the escrowed funds if someone redeems before anticipated.

My brother and I cashed out of our 5-plex in Ballard last NOV and moved our funds to a property in Boise, ID. 

It all depends on the county’s tax rate, school system, towns budget, land value and acreage, home value etc.

I've secured funding for single family investments, but have yet to pull the trigger.

Either into another property or in the index fund like you’re talking about.    

We have plenty of poor rating schools here where the students can not even write proper English.  

I am currently self funded and struggling haha.

But if you don't have enough to cover expenses, can you fund the expenses from non-IRA accounts?