The closest I have found is Zillows rent Zestimate but accuracy is a concern.I'm trying to avoid:1.

Is he deciding between Bloomington and Indy or is he definitely moving to Bloomington and Indy's just the closest large city to name?

My recommendation is to call the base operator where his military unit is and get the number to the closest JAG office.

@Ash Badry My preferred markets are BC (because it's closest to home), NB (low prices) and MTL (due to my sister living there).

One of my closest friends works for Solar City and is guiding me toward this process with my rentals and my own home. 

I also called near by compatible for rent signs, I was about $150 higher than the closest property for rent which did concern me a little, but I had a flood of calls and rented very fast.  

You could even find out how far it is to the closest point the free Google or Yahoo, etc., buses will pick up workers and include that in your ads.BTW, I used to manage a 26 unit building in Santa Clara - retired November 2013, so I'm pretty familiar with that market.

For instance where I live, the closest Craigslist section is for Eureka, which is an hour and a half away. 

The closest I've come to doing this, is I improved a lot by putting in a driveway, fence, septic and well. 

Sometimes the closest one brings out his big screen tv and they all hang out around the pit and watch a game or talk to each other.