That machine has to have the rope pulled once to charge the capacitor that turns the fuel pump but it should start on the second pull. If the fuel rail looses pressure after sitting then it will take more than that. That may be your issue.
There is a white connector on the left front side just ahead of the belt guard that is the fuel pump prime. Wires should be brown and solid red. You can apply 12 volts to that connector and power the pump. Try that and see if it will start on the first or second pull.
Loss of fuel pressure after sitting won't be much to worry about but if it does it after sitting for a short while then you need to worry. The fuel rail has a pressure regulator on it that may be the issue or the fuel pump. Both hold the pressure in the rail when it isn't running. Also look for leaks in the fuel lines and filter. They need to be good for it to hold pressure.
