If they could instead pay $1,000 for first month's rent and a $15 monthly fee, suddenly it's affordable for a lot more people.

Well, I'm going to guess you will find more affordable starter-investments in Kenosha than you will in Chicagoland or, do you just prefer to drive north instead of south!!!

For example, someone might buy a property that E5 and above to afford while someone else focuses on the higher end of the market..say senior enlisted and officer grades. 

I'm also able to afford a much more expensive property by paying less out of pocket.Prices are at a point where it would make it hard (not impossible) to find a property that cash flows with a VA loan (no money down).

You'd probably be able to afford upgrading your primary residence and owning a small vacation rental somewhere, now throw in some extra income from that vacation rental and you should be in pretty good shape. 

She wasn't going to be back for two more months (traveling nurse) and couldn't afford to pay the rent.

I came across a property that is right now for sale 200k 13 unit property, and I came to about 4-500k all in with repairs and renovations I would like to purchase this property but I know my funds would come up just shy of being able to afford this if I went the conventional route.

And the ability to complete of manage rehabs is an extremely rare and valuable skill.I would recommend evaluating whether multi or single family rentals work in your market, then determine which is more affordable compared to what offers the most cash flow.

There are some nice burgeoning areas of Austin with relatively affordable prices that are worth considering.  

After your loan officer gives you a good estimate for how much house you can afford, go on the hunt!