I've searched for older threads relating to this problem and they are similar but not exactly the same to the issues I am having. I have a 68 Cutlass Supreme and if I let it sit for a few days without starting or in cold mornings/freezing nights it takes at least 5-10 tries and a few pumps to get it started. Once it starts I give it a little gas and it idles and drives fine. It will also restart instantly on first try after that as long as the engine is warm. The battery has died on me twice from so much cranking and little driving since I only have been warming it up and driving it around the block once or twice a week.

The other threads said it might be a fuel pump issue? I see fuel in the filter and it drives fine after its been started. Any suggestions? Would it be worth buying a new $20 mechanical fuel pump and 20 minutes to change out? I don't know a lot about the history of the car but it's overall pretty well kept for its age.

 

Check the rubber flex lines at the pump, behind the front wheel in the frame and at the tank. If they are original they will be cracked and the pump will be sucking air...