I have always worked on the the following rough guide.
As Sam said, trips, to my mind, are rated on what car can complete the trip rather than what I think a driver is capable of, because that's too hard to anticipate.
I am confident that if the dynamic of the trip is right, no one will crack it and we will keep the group moving, even if a member actually thinks the track is beyond them. I don't think this is possible to totally avoid.
Easy - Lots of bypasses, no serious chance of significant vehicle damage for a standard vehicle. low likelihood of recovery.
Medium - Maybe some technical bypasses or some moderately difficult sections of track that can't be bypassed, but for a reasonably driven car, low likelihood of damage. Standard vehicle still able to drive the day. Recovery may be likely for more standard cars, but the trip should not involve any seriously risky lines etc.
Hard- Day is predominantly about technical driving. Likely to be no bypasses for difficult sections of track. Damage is possible even for a skilled driver. Aftermarket equipment such as gearing and locking diffs recommended.
The catch is that some of us will find every opportunity to turn an easy trip into a hard trip

and we all know someone who runs hard trips in a nearly stock car and does fine.
We are a small group and will always have a diverse range of drivers and cars on any one trip. I wouldn't run any trip that didn't allow some opportunity to play, as that discriminates against more experienced/advanced members and will then mean they don't participate, reducing the number of cars on trips and limiting their feasibility.
I can't help that new members significantly underestimate the ability of their vehicles and their driving ability.
The problem with making ore complex trip ratings is the possibility that one persons 8 is another persons 6.... Its almost 100% interpretive. When I run a trip I am confident that once I know who is going we can run a route that will work with the group that's coming. I will tune the route to the group that signs up. That might mean that a trip that was advertised as a 5 might become a 7 if the group is right, or vice versa. I like that a lot about our club, but it works against complex trip rating schemes.
No offence intended, but the fact is that new members generally have a poor conception of what a trip rating is and so I don't get too hung up on a new member coming to me after a trip and saying "that wasn't easy/medium" - sure, it might not have been for them, but that's what I call an easy/medium trip and all of mine will be like that. I can't run a trip that's easy medium in the eyes of a new member because I don't know what they're expecting.
Steve.