Still not sure what's going on with the dates. Everything was working fine in FTM 2012 (Windows) but after I converted to Mac, they haven't.
I went ahead of updated my facts. Instead of Military (Jan 1, 2010-Dec 31, 2010), I have Military Enlistment (Jan 1, 2010) and Military Discharge (Dec 31, 2010).
I really liked using date ranges, but for some reason FTMM2 isn't working for me.