I partner with a rockstar contractor and a top level investor friendly agent and if we buy right and nail our numbers, there is plenty to split at the end.  

The one thing to consider is that IL and NY are both not landlord friendly states.

In 2008 a friend of mine spend $300,000 to buy 100 houses in Detroit.  

Quote from @Colby Burns: You can also partner with an Investor friendly Realtor who has a team of PMs, GCs etc for you.  

What educational real estate avenues are GI Bill friendly?

I'm up at Lake Tahoe in the basin and there are many CA investors that have been investing in Reno, NV because of the low taxes, landlord friendly, and only 30 minutes from Truckee.

Has owner financing come up in your conversations with your friend from church?

I make about 70k a year from my salaried job and my friend makes double that.

Google is your friend on this one.

I've read BiggerPockets' Real Estate Investing book and am particularly interested in the house hacking strategy, as I'd like to move out of my current living situation.Our main dilemma is choosing between a single-family home (renting out one room to a close friend) or a multifamily property like a duplex or triplex.