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

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.

While I know this isn't a lot in today's market, I believe there are creative ways to make it work.I’m a former foster child who was declared independent as a teen, so I've been living with close friends that I consider family.

Google is your friend on this one.

Check out FilePlace, where user-created forms are available for free.

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.