Alright. completely shifting gears here lol.. Turns out every time I was pulling the regulator, the battery was also dead from trying to start the car while broken down. I have verified that the problem is not fuel related. The problem is electrical related. It can be fixed by removing the power from the system for a brief moment, then reconnecting it (Hence why killing the battery would solve the problem). I swapped PCMs from my GTP and put the tune on it and it seemed to help, but it still happened.
*OLD * I've been having really strange issues with the fuel system lately. I'll be driving down the road and out of nowhere the car will suddenly lose all its power, shut down and not want to start again after that. If I try to restart it, it just stumbles for a bit and doesn't ever grab and start back up.. I have 60# Injectors on the stock rail but I drove about 1,000 miles until this happened. Since, I've replaced the fuel pump, fuel pressure regulator, and now the fuel rail itself with another in case I had some issue there, but the problem still persists. If I remove the fuel pressure regulator and put it back in just right, the car will start back up, but will repeat the problem not too long after. Any suggestions?