Update September 24th 2017:

After many many hours actually days of trying, searching, data recovery attempts and Brute Force... still no luck! I talked with my dad for hours and hours about that fateful night and It turns out the #1 Json file was never saved. He saved a link to the download page repeatedly to his desktop and thought that he was saving the Json file. Masive data recovery attempts have only lead us to believe the Json file was never downloaded at all.
#3 Json file with the password that simply does not work is confusing us. We've had strange success at unlocking it sort of if I put in the password in backwards. After a lot of research about the subject my conclusion is that we've stumbled on to a password that actually De Crips the encrypted private key but only for a different public address that has a zero balance. We have a cryptocurrency expert running Brute Force with no luck yet.