I can help you get the field close to equal in Gran Turismo mode if you give me some guidelines to follow. I know these cars pretty well and have the time that maybe some others don't.
In past versions of Gran Turismo, I have made cars very close in the power:weight category but never hosted an online league. I'm willing to use this experience and help you get this series off the ground.
What I'm thinking off the top of my head:
Cars with bigger displacement engines (circa 350-400 and up cubic inches) should suffer in one way or another. The 440 equipped Charger will eat a 289 Shelby or 302 cubic inch Z/28 down the straights no problem. I'm thinking that brakes, suspension and weight could be used to penalize/reward cars that vary power wise.
What cars are legal for your competition? Trans-Am started in 1966
http://www.trans-amseries.com/TransAm101/History.asp with the hottest years coming between 1968-1972. In fact, a number of years ago, there was going to be a video game released titled, "Trans-Am Racing '68 - '72." It got shelved before it could get released
http://sgn.cc/racing/trans_am_racing/interview1.shtml If you are interested, you should check out the book written about the early T-A years
Are you aiming to get cars equal in the power:weight ratio? I can experiment and find out how much weight gets taken off a car for each stage of weight reduction. From there I can get back to you and you/we can decide which cars get what amount of weight reduction.
Do you want cages in all cars?
Is there any part, such as brakes, that you would like all cars to have equipped?
Would you use "rewards weight" and add ballast to the top 5 finishers and subtract weight for the bottom .... 5? 7? (Depending upon how many entrants you have).
Do you want to run all cars in one class? Would you be willing to break cars up into "under 2L" and "over 2L" classes? It's awful hard to get a 1.8L anything to compete with a 4.7L Shelby GT350, let alone a car with more engine than that. Big blocks may not corner as well as a lighter car, but some corners can be taken at 30 MPH tops and even the big block cars can get around at that speed. In those cases the big blocks are in a win-loss-tie-win (straightaway speed, braking distance, cornering speed, exit speed) situation. The GT350 and Z/28 would be in a win-win-win-win situation in that regard because those cars are just powerful small blocks that can do a lot of everything well.
That's about all I have for now. Post your replies and we can get started in the equalization of the cars.