So say you try to start it 4-5 times like you have been, if you unscrew the fuel filter off after doing this is it still full? Depending on where your leaking at, and not knowing how well some other things on your engine are operating for easy starts it might not hurt to make sure that after you crank it for a while your not draining back to the tank for example.
Just trying to rule out some of the easy things before you move on to the next stuff. My return lines leaked so bad on mine for air that if I parked it nose up when I first got it, all of my fuel from the IP and fuel filter and lift pump would drain back towards the tank and it just wouldn't run until I manually filled everything back up via squirt bottle. Plugging in the block heater for two hours made the oil warm enough that it would spin faster and help itself sometimes to re prime but not always. Eventually it was time for new return lines and olives and no issues since.