As the saying goes, "There is no replacement for experience," but on the flip-side, how are you supposed to get the experience if you don't try? It sounds like the client is a very understanding guy and this is a great car for you to really hone in your correction skills on truly hammered hard paint. I will do my best to help.
People were certainly doing paint correction before paint thickness gauges became common they are not a necessity, but you are 'shooting in the dark' with out one.
So while I am not recommending that you don't correct the paint, I would caution against chasing every scratch and defect in trying to create a perfect finish. A true professional (IMO) knows the limitations of what he can safely accomplish. By chasing every visible defect known with out the tools and experience necessary to know when to back off you run the risk of overly thinning the clear coat or worse, striking through it.
Removing too much of the clear (even if you don't burn through it) can lead to medium and long term problems and it is your job to know when to say when.
Also it is almost impossible to know whether or not the car has been polished (and to what degree) in the past. Many cars are polished to some degree at the factory, most car dealers while grind through paint with out care, etc. Look for any compound residue that has splattered in weird areas, holograms in the paint, burnt edges, etc. (Note the car appears to have severe holograms behind the red slashes in the pic posted above) I wouldn't risk my reputation on a guess, I would caution you against it as well. (In the end it is going to be far worse to burn through then not get every possible defect).
Aggressive is relative to what you are working on. If you are concerned about the marks that you may leave behind from a wool pad/rotary then I would absolutely recommend that you do not sand the car. It takes experience and skill to create a perfect finish and trying to run before you can walk can lead to a lot of frustration and disastrous results.
I think your approach to this point has been spot on. You did get aggressive with your application (compound x2) but you haven't over stepped your comfort zone. Thus you have improved the finish with out comprimising it, and that is a hallmark of a professional. The true pro isn't the one who makes paint look perfect, it is the one who maintains the integrity of the automobile and preserves the finish. [/FONT][/COLOR]
How comfortable are you getting more aggressive on this finish? Is the risk worth the reward? I am sorry I keep repeating my point, it is only that at the end of the day it is you, your client, and his car, and you are ultimately responsible for all three. I would be easy for me to tell you to get more aggressive but I don't have to face your client if you screw up.
It is hard to prescribe a process because processes because individual technique is such a huge equation in the factor. What works for you may not work for me and vice-a-versa.
If you are truly not happy with the results of your process and feel you want to try to improve the finish that I feel it will be better to cover some basic points that will help you dial in the best process for your technique.
-Start with the least aggressive method necessary- Since you have already attempted a fairly aggressive technique, we know that we are going to need something more aggressive.
-Do a test section and inspect the results of that test section after each process-
So set up your test section, and dial in the least aggressive method you need to remove the defects. The goal is to remove all of the defects you plan on removing in this stage, don't count on the follow up stages to remove anything left behind.
Once you have achieved the desired amount of defect removal wipe the surface with alcohol and inspect in any form of light available (if it means pulling it out in the sun then do so.)
Again start with the least aggressive method necessary to remove the swirling caused by the more aggressive method. Every paint responds differently to a compound and wool pad, but the goal is to remove the marks completely and hopefully get the surface ready for final polishing. Some cars may need more then three stages, so starting with the least aggressive method and constantly inspecting the finish as you go is going to be your best bet.
Wipe with alcohol and inspect the finish again. If it is ready for final polishing then proceed.
You will now have dialed in a process then will work on the majority of the paint. The goal is always to use the least aggressive method to get the results you are after.
Corvette's (C5/C6) tend to have pretty hard paint although I wouldn't say they are anywhere near the hardest paints I have ever corrected. Since there is no way to identify how deep the defects are or how much paint is on the surface I would strongly consider a conservative approach. I would explain to your client that the defects are very deep and that you don't want to compromise his paint by making things perfect. The worst thing you can do is give him unrealistic expectations and damage the paint in attempt to meet those expectations.
I hope I helped and best of luck!
Todd