Since you are frustrated, and the Great Guy seems overwhelmed, you should take it upon yourself to try to “unoverwhelm” him. Start by asking the operator whether (and how) you personally can help. Then see whether others in your league can help lighten the load.

Depending on the structure of your league play, and on the attitudes of the players, it may make sense to mix business and pleasure and work on machines during your league play time. Otherwise selecting a different weekly occasion might make sense (with a smaller, more motivated group). If you’re not looking at a large, heavily played collection (i.e., home vs. arcade) you could, for example, shoot for one machine repaired and shopped out every week until the whole herd is in order. The group could choose the machine, and list all known issues.

If the operator knows you, he’ll probably welcome the help. But if he insists on doing everything himself, but doesn’t, you’ll have to decide whether the league play is worth the frustration.