I played Mafia 3 years ago twice. In this game you have to complete the game two times to get all the achievements with completely different choices. As I said I already did that and thought to myself just play the game a bit more to get the rest of the miscellaneous achievements and 100% it.
Well, apparently the game has a serious achievement tracking problem, any action that requires you to do the same thing multiple times, including those various choices, has to be done in a single game session. When you close the game it magically forgets the things you've done and you have to do them all over again.
I'm just writing this so you guys know and beware, I loved the game but for achievement hunters like myself it was a pain. I had to resort to other people's save files to get the No Loose End achievement you see above