Ok, so, I found out what my problem was. The first time around I did all Gigs and Blue Markers, but the trophy failed to pop and I didn't have a save to reload and try again.
The second time around, 2 GiGs would not spawn for me: Fixer, Merc, Soldier, Spy and Small Man, Big Evil. Those 2 GiGs are related to another one called Welcome to America.
If you don't have those 2 gigs in your log, go do Welcome to America, and if you already did, go to the docks where the car was, and if the car is STILL there, your quest is bugged and you'll have to start over.
Make sure Regina calls you as you near EVERY gig, and after you finish EVERY gig. If she's not calling you, do a side job to trigger the end of PSYCHO KILLER as that quest is also bugged.
For Blue Markers, you need to make sure the JOB COMPLETE message pops on the left side, and if its a Blue "?" " make sure you grab the followup quest from that.