My knowledge is not great either, but I dealt with an oldsmobile like this in my high school auto shop. It was the same way it wouldnt start without some help (carb cleaner) and after running off carb cleaner for a while it would fire. Our teacher told is it was probably a bad fuel pressure regulator, or that there was a leak somewhere else in the line causing the system to loose pressure after each use. Normally fuel systems stay pressurized. I know the fuel pressure regulators on these trucks are the topic of much discussion. So maybe you could start there? Good luck.