Hate to say, or ask this but I wonder what the age of the OP is? We get plenty of older guys come into the store complaining that a saw is "hard to pull over" and there must be something wrong with it. Sadly, the problem is that these guys have reached a point where they can no longer snap the rope enough to start the saw. Kind of a delicate thing to communicate to the customer without offending them. Whether we start the saw or ask them to try it, you don't want to make them feel like crap. Best to say "we" are all getting older. This problem is worse for someone who might go a long time between saw use, vs someone who runs a saw all the time.
Dad just gave me his farm use saw due to such 2 winters ago. Age and bad shoulder caught up to him.
It's gonna catch us all. Did you come up with an alternative for him? Soomething smaller and easier to start. My Dad is 90 and can still start the 350 I leave at his house. Some customers have gone the battery route. The little 120i runs with only the smallest gas saws, but it does more work than a saw that they can't get going. Keeps the guys out and active too.