[tomwed]

One of the downsides of planning a large outing is that everyone finishes at a different time. This makes going out for food or drinks less convenient.

What if the executive courses on a rotating basis had a shotgun start at 6:30pm [or earlier 5pm?]. Golfers would all finish at 8 pm [or 6:30 pm]. That's a nice time of the day to play in hot weather and the courses are thinning out.

A group of 20 could sign up for 5 tees.

I don't think it would be much of a software change. Maybe a programmer could chime in.