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Only way to really know is if you have all or most of the records of the car. When I bought mine, the previous owner had kept all of the records/receipts and gave them to me. I can tell you who all three of the previous owners are, who they worked for when they bought the car, and what their home address was when they owned it.
In fact, I just organized all of the receipts the other week. I went through all of them and sorted them by date and then placed them in a 3-ring binder. Makes it so much easier to find past info on it.
Folks I know approach it from both ends, but it's often a long, drawn out process.
From the beginning
Any C4 owner can get the original dealer off the window sticker (available from the National Corvette Museum). I've known people who call the original dealer, leave their phone number or address and ask the dealer to contact the original owner. If the dealer still has the original paperwork, you actually have fairly decent odds that the original owner will get in touch with you (they're often curious about where their baby ended up). From there, you can start tracking forward.
From the end
When I purchased my Corvette from a dealer, the title still had some of the previous owner's information on it. I believe this is often true and it certain help me start tracking back over my four owners.
A shot in the dark
The NCRS Driveline will accept ads from NCRS members asking for information on a certain VIN. I'm told that the response rate is surprisingly (almost scarily) high ...
Don't forget to do a thorough search under the seats and console where bits of paper may have gotten lost and overlooked. I've found many previous owners this way.
Ok this was a hassle but I did a carfax found out where car was registered my insurance agent found out his agent and had his agent leave a message to call me if he could and told him why.The ins. guys cannot give out this info but if you are friendly with them they can find out and do it this way. the privacy laws restrict them from telling you names. But it worked the guy did get in touch with me.
I know it's not right, but when I purchased my GMC Yukon as a repo, I told the Chevy parts about not wanting to be anywhere near the previous (guy who was repo'd) area. They told me his name and address.
So much for keeping the data secret...